b n hinesol.mswdWDBNMSWDuwKm 7#      ..\\\\ f pp:x\" Bi* iZii5iiiiii u CHMDGrphbjdCHMD epi-Hinesol-1dCHMDHH(FG(HH(d'`CH3D=$Grphbj HHdjCD3DDPRFd )$zX dCH3DPY*+symbCCCCCCCCCCCCCOCCHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHHXHXHXHXHXHXcartJȂ 3f=1oiHZĈ7O>JƾcBXf?%~hX5}q{H0OG{2)^vގD{Re{Tl>ZT, VB4) 3(#dO"ZuGI .?mMWBAFۋ Y ( 4D@xh(W0[X &)W +k]\5 *lbond % #   "        ! &$'()   ; : currentpoint !Q"osss#Q"p!sss#Q"Y7sss#Q"d)()(#Q"[sss#Q"sss#"e(#"e(Q#"4'sss#)()("osss#"j # "j# Q"sss#Q"=sss#"< # "< # "<#"T#"#"#"+#"+Q#"sss#"x # "x#"a # "a#"8 # "8Q#"sss#Q"sss#Q"`sss#Q"Tsss#"Q#sss"Q#sss" # "Q#sss"xQ#sss"O#"OQ#sss"cQ#sss"cQ#sss"[Q# sss"[Q#T/dict3D 110 dict def dict3D begin % Copyright 1986-92 Cambridge Scientific Computing, Inc. /b{bind def}bind def/l{load def}b/X/translate l/R/rotate l/S/scale l/N/newpath l/gs/gsave l/gr/grestore l/e/exch l/r/roll l/p/pop l/s/sub l/d/div l/a/add l/m/mul l/D/dup l/L/lineto l/M/moveto l/A/arc l /C matrix def/E{X R 1 S 0 0 5 2 r arc C setmatrix}b/x{e def}b/G{64. d setgray 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g}if{{P}{{{DS}{DD}{gs 12 OB np bW 2 dv/bd x lW 2 dv e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b "<Mq&L=N=N=L&L&N=N"H_q">LIaHaIaI`>L>NHa"Ha"&t")p"a qa'uaa&u'ta"'MqL'aaa'N'La"iTq"VMkUjUkTkTVMVOjU"kjq"jTlkjklklUkTjUjk"VrqTlltWqTtlljlWq"Uqq"I`WtTtWqI`IaIbTt"J^"KZ"MX"PU"RS"TP"|Eq&kD~U~G|G|DkTkTlU~G"Jq"|EKKJ~E|E~GK"y3q"x3}Fz3x3{D{F}Dz3"<"D">J"@F"BC"E@"G=q&f`ff``p__"q""q"" "q""########"########" q""""""""q"&q'&'&" """ q"q"""""'#####""" "#"%q 8F F8 : 8 F" 8"v"%" " "q"" q"" ""q"#!#!"s"p"m"!j"$g" " q"q"yqy~zy~~z"| q     " "2qs1331s1s33"Dq"1FFFE13F"Y "U "sY"hF "t2q"h1tFhDhFiFt3t1hD"f"/"+"("%"""_Q"EP qDPSVFPDPSVSUFP"E:qD:FQF:D:DQFQF:end %%EndProcSet 40 60 28 20 60 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 534 687 3 5 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C np 1554 1216 M 1526 1232 l 1526 762 l 1554 778 l cp f np 1933 1435 M 1933 1451 l 1926 1463 l 1526 1232 l 1554 1216 l cp f np 2313 1216 M 2327 1224 l 2327 1240 l 1960 1452 l 1933 1451 l 1933 1435 l cp f np 2313 778 M 2341 762 l 2341 1216 l 2327 1224 l 2313 1216 l cp f np 2231 818 M 2259 818 l 2259 1177 l 2231 1177 l cp f np 1933 558 M 1933 526 l 2341 762 l 2313 778 l cp f np 1933 526 M 1933 558 l 1554 778 l 1526 762 l cp f np 1697 2129 M 1687 2143 l 1672 2139 l 1546 1712 l 1572 1704 l cp f np 2131 2129 M 2151 2157 l 1694 2157 l 1687 2143 l 1697 2129 l cp f np 2265 1744 M 2319 1672 l 2151 2157 l 2131 2129 l cp f np 2319 1672 M 2265 1744 l 1925 1462 l 1933 1451 l 1960 1452 l cp f[1 4 1887 1483 1605 1676 ]Bd np 1420 2525 M 1392 2488 l 1351 2466 l 1672 2139 l 1687 2143 l 1694 2157 l cp f np 1501 2756 M 1475 2766 l 1387 2516 l 1392 2488 l 1420 2525 l cp f np 1021 2433 M 1027 2405 l 1351 2466 l 1392 2488 l 1366 2498 l cp f np 1215 2726 M 1193 2708 l 1366 2498 l 1392 2488 l 1387 2516 l cp f np 2594 1362 M 2580 1386 l 2327 1240 l 2327 1224 l 2341 1216 l cp f[1 4 1489 1253 1230 1403 ]Bd 65535 0 0 C 7040 4050 380 170 43 Ar 0 0 0 C np 8446 2996 M 8452 2962 l 8770 3300 l 8760 3310 l 8743 3312 l cp f np 8044 3186 M 8032 3160 l 8452 2962 l 8446 2996 l cp f np 8536 3692 M 8550 3724 l 8093 3638 l 8099 3610 l cp f np 8550 3724 M 8536 3692 l 8743 3312 l 8760 3310 l 8761 3338 l cp f np 9451 3535 M 9459 3561 l 8984 3707 l 9058 3655 l cp f np 9016 2959 M 9026 2933 l 9460 3081 l 9450 3107 l cp f[1 9 8038 3173 8096 3624 ]Bd [1 9 9455 3548 9455 3094 ]Bd np 9058 3655 M 8984 3707 l 8761 3338 l 8760 3310 l 8771 3302 l cp f[1 4 8797 3258 8984 2998 ]Bd np 2914 5656 M 2886 5672 l 2886 5202 l 2914 5218 l cp f np 3293 5875 M 3293 5907 l 2886 5672 l 2914 5656 l cp f np 3673 5656 M 3687 5664 l 3687 5680 l 3293 5907 l 3293 5875 l cp f np 3673 5218 M 3701 5202 l 3701 5656 l 3687 5664 l 3673 5656 l cp f np 3591 5258 M 3619 5258 l 3619 5617 l 3591 5617 l cp f np 3293 4998 M 3293 4966 l 3701 5202 l 3673 5218 l cp f np 3293 4966 M 3293 4998 l 2914 5218 l 2886 5202 l cp f np 3238 4650 M 3266 4650 l 3266 5005 l 3238 5005 l cp f np 3320 4650 M 3348 4650 l 3348 5005 l 3320 5005 l cp f np 3954 5802 M 3940 5826 l 3687 5680 l 3687 5664 l 3701 5656 l cp f[1 9 3293 5891 3293 6200 ]Bd [1 4 2849 5693 2590 5843 ]Bd 6520 5370 4380 5370 2 Ar np 7504 5636 M 7476 5652 l 7476 5182 l 7504 5198 l cp f np 7883 5855 M 7883 5871 l 7869 5879 l 7476 5652 l 7504 5636 l cp f np 8263 5636 M 8277 5644 l 8277 5660 l 7897 5879 l 7883 5871 l 7883 5855 l cp f np 8188 5585 M 8202 5609 l 7890 5788 l 7876 5764 l cp f np 8263 5198 M 8291 5182 l 8291 5636 l 8277 5644 l 8263 5636 l cp f np 7883 4978 M 7883 4962 l 7908 4960 l 8291 5182 l 8263 5198 l cp f np 7858 4960 M 7883 4962 l 7883 4978 l 7504 5198 l 7476 5182 l cp f np 8551 5786 M 8537 5810 l 8277 5660 l 8277 5644 l 8291 5636 l cp f[1 4 7440 5673 7187 5819 ]Bd np 8121 4767 M 8137 4789 l 7908 4960 l 7883 4962 l 7883 4945 l cp f np 8090 4274 M 8110 4246 l 8209 4534 l 8183 4544 l cp f np 7656 4274 M 7636 4246 l 8110 4246 l 8090 4274 l cp f np 7569 4554 M 7543 4546 l 7636 4246 l 7656 4274 l cp f np 7602 4773 M 7618 4751 l 7883 4945 l 7883 4962 l 7858 4960 l cp f 10780 5410 9000 5410 2 Ar np 1014 7876 M 986 7892 l 986 7422 l 1014 7438 l cp f np 1393 8095 M 1393 8111 l 1379 8119 l 986 7892 l 1014 7876 l cp f np 1773 7876 M 1787 7884 l 1787 7900 l 1407 8119 l 1393 8111 l 1393 8095 l cp f np 1698 7825 M 1712 7849 l 1400 8028 l 1386 8004 l cp f np 1773 7438 M 1801 7422 l 1801 7876 l 1787 7884 l 1773 7876 l cp f np 1393 7218 M 1393 7202 l 1418 7200 l 1801 7422 l 1773 7438 l cp f np 1368 7200 M 1393 7202 l 1393 7218 l 1014 7438 l 986 7422 l cp f np 2054 8022 M 2040 8046 l 1787 7900 l 1787 7884 l 1801 7876 l cp f[1 4 949 7913 690 8063 ]Bd np 1623 7013 M 1639 7035 l 1418 7200 l 1393 7202 l 1393 7185 l cp f np 1600 6514 M 1620 6486 l 1720 6777 l 1694 6787 l cp f np 1166 6514 M 1146 6486 l 1620 6486 l 1600 6514 l cp "R5qD5T9T6S5D9F9T6"^9 q"^8hF_8^9gFhFhD_8qpx t xtpt "s"~6qh5775h5h77"Iq5JJJ57J"] "h]"kY"]J q\Ji^^J\Jh^i]^J"i6q\5iJ\J^Ji7i5\J"j"3"/",")"&"E"K"G"MG"MKq/7373/3 22"<"G"< "&q"&<&&<<<&"(" q%%%"%q&&%"Dq"<ECE=<<C"="?"A"C"F"]q"H^^^HHH^" q    " "gq_hgh__gq-z515z1|-z1"0z"4q5555"@q"6A@AA66@"@q&5A567AA@5""!" "q"6 q"5>=>765="7"8":"<"="?"W"""a"4q"&555&&&5 f np 1080 6791 M 1054 6783 l 1146 6486 l 1166 6514 l cp f np 1122 7020 M 1138 6998 l 1393 7185 l 1393 7202 l 1368 7200 l cp f 5340 7430 2760 7430 2 Ar np 6214 7656 M 6186 7672 l 6186 7202 l 6214 7218 l cp f np 6593 7875 M 6593 7907 l 6186 7672 l 6214 7656 l cp f np 6973 7656 M 6987 7664 l 6987 7680 l 6593 7907 l 6593 7875 l cp f np 6973 7218 M 7001 7202 l 7001 7656 l 6987 7664 l 6973 7656 l cp f np 6891 7258 M 6919 7258 l 6919 7617 l 6891 7617 l cp f np 6593 6998 M 6593 6966 l 7001 7202 l 6973 7218 l cp f np 6593 6966 M 6593 6998 l 6214 7218 l 6186 7202 l cp f np 7254 7802 M 7240 7826 l 6987 7680 l 6987 7664 l 7001 7656 l cp f[1 4 6149 7693 5890 7843 ]Bd np 1407 8420 M 1379 8420 l 1379 8119 l 1393 8111 l 1407 8119 l cp f np 6648 8345 M 6620 8345 l 6620 7868 l 6648 7868 l cp f np 6566 8345 M 6538 8345 l 6538 7868 l 6566 7868 l cp f np 6538 6650 M 6566 6650 l 6566 7005 l 6538 7005 l cp f np 6620 6650 M 6648 6650 l 6648 7005 l 6620 7005 l cp f 3400 11250 120 11250 2 Ar np 4224 11436 M 4196 11452 l 4196 10982 l 4224 10998 l cp f np 4603 11655 M 4603 11671 l 4589 11679 l 4196 11452 l 4224 11436 l cp f np 4983 11436 M 4997 11444 l 4997 11460 l 4617 11679 l 4603 11671 l 4603 11655 l cp f np 4983 10998 M 5011 10982 l 5011 11436 l 4997 11444 l 4983 11436 l cp f np 4901 11038 M 4929 11038 l 4929 11397 l 4901 11397 l cp f np 4603 10778 M 4603 10746 l 5011 10982 l 4983 10998 l cp f np 4603 10746 M 4603 10778 l 4224 10998 l 4196 10982 l cp f np 5271 11586 M 5257 11610 l 4997 11460 l 4997 11444 l 5011 11436 l cp f[1 4 4160 11473 3907 11619 ]Bd np 4617 12118 M 4589 12132 l 4589 11679 l 4603 11671 l 4617 11679 l cp f np 4548 10430 M 4576 10430 l 4576 10785 l 4548 10785 l cp f np 4630 10430 M 4658 10430 l 4658 10785 l 4630 10785 l cp f np 4851 12302 M 4833 12324 l 4589 12132 l 4617 12118 l cp f 7840 11210 5740 11210 2 Ar np 8194 11306 M 8166 11322 l 8166 10852 l 8194 10868 l cp f np 8573 11525 M 8573 11541 l 8559 11549 l 8166 11322 l 8194 11306 l cp f np 8953 11306 M 8967 11314 l 8967 11330 l 8587 11549 l 8573 11541 l 8573 11525 l cp f np 8953 10868 M 8981 10852 l 8981 11306 l 8967 11314 l 8953 11306 l cp f np 8871 10908 M 8899 10908 l 8899 11267 l 8871 11267 l cp f np 8573 10648 M 8573 10616 l 8981 10852 l 8953 10868 l cp f np 8573 10616 M 8573 10648 l 8194 10868 l 8166 10852 l cp f np 9238 11454 M 9224 11478 l 8967 11330 l 8967 11314 l 8981 11306 l cp f[1 4 8128 11344 7865 11495 ]Bd np 8587 11988 M 8559 12002 l 8559 11549 l 8573 11541 l 8587 11549 l cp f np 8518 10290 M 8546 10290 l 8546 10655 l 8518 10655 l cp f np 8600 10290 M 8628 10290 l 8628 10655 l 8600 10655 l cp f np 8823 12173 M 8805 12195 l 8559 12002 l 8587 11988 l cp f np 7897 6180 M 7869 6180 l 7869 5879 l 7883 5871 l 7897 5879 l cp f gr count origstk sub{P}rp end chemsave restore ,  Helvetica .+HCH +3 (}H *+ 3 +(})C+HO(MCH +3 (M%H *+ 3 +(M3C+mO+'DCH +3 (BCOOEt(+iH *+ 3 +(+wC(*CH +3 (ACOOEt(*OH *+ 3 +(*]C(O(sO(hCH +3 (ACH +2 `(WOH( H *+ 3 +(C(_SO(_.O(lCH +3 (H *+ 3 +(C(\epiր)-Hinesol+،O(L CH +3 (LH *+ 3 +(LC, Geneva ( Synthesis: (!oP. DesLongchamps * Can. J. Chem.ڀ)O, (1980), 2460.(O(gxThis is an example of a * compound of the spirane * class.(q CH(COOEt) +@2 ( Ethylene glycol+ Tosic acid(LiAlH -+4 (FCH +3 (FqH *+ 3 +(FC() 1. Na/ EtOH(gHCl(O(11. Ketal formation and use as protecting group. * &2. Isomerization with enone systems. * I3. Lithium aluminum hydride, structure, reactivity, reaction conditions * 4. Deprotection and mechanism(jCH +2 `(j-COOH(B2. Diethylmalonate(%+ HCl, reflux($5. Formation of the malonate anion * 6. Malonic ester synthesis * M7. !,4- additions, Michael Reactions, examination of HOMO-LUMO interactions * 48. Hydrolysis and decarboxylation of malonic estersd-CHMDSTRG  x(<< q&=$ $=CH3D=$Grphbj HHUdjCD3DDPRFd )$zX dCH3DPY*+symbCCCCCCCCCCCCCOCCHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHHXHXHXHXHXHXcartJȂ 3f=1oiHZĈ7O>JƾcBXf?%~hX5}q{H0OG{2)^vގD{Re{Tl>ZT, VB4) 3(#dO"ZuGI .?mMWBAFۋ Y ( 4D@xh(W0[X &)W +k]\5 *lbond % #   "        ! &$'()   =$ >% currentpoint !>%Q"sss#Q"sss#Q" sss# Q"U )()(# Q" sss# Q"sss#"#" Q# "hsss#)()("E sss# "#"#Q"A sss# Q"vsss#"u#"u#"u#" # "#" # "Y # "YQ#"Bsss#"\#"\#"#"#"n#"nQ#"sss#Q"sss#Q"f sss# Q"q sss# "FQ#sss"FQ# sss"#"Q#sss"Q#sss" # " Q# sss"`Q#sss"`Q# sss"y Q#sss"yQ#T/dict3D 110 dict def dict3D begin % Copyright 1986-92 Cambridge Scientific Computing, Inc. /b{bind def}bind def/l{load def}b/X/translate l/R/rotate l/S/scale l/N/newpath l/gs/gsave l/gr/grestore l/e/exch l/r/roll l/p/pop l/s/sub l/d/div l/a/add l/m/mul l/D/dup l/L/lineto l/M/moveto l/A/arc l /C matrix def/E{X R 1 S 0 0 5 2 r arc C setmatrix}b/x{e def}b/G{64. d setgray fill}b /RGB{setrgbcolor}b /fB{closepath gs P fill gr stroke}b/pS 8 string def/pF 4.5 0 C defaultmatrix dtransform D 0 ne{e}if p D 9. d round d def/pA 1 0 C currentmatrix dtransform e atan def/pt{pS copy p pF pA{1 a 4 m cvi pS e get e 1 a 4 m cvi 7 s bitshift 1 and}setscreen 0 pS{8{D 1 and 3 -1 r a e -1 bitshift}repeat p}forall -64. d 1 a setgray}b/jn 80 string def/nL statusdict/jobname get jn copy length def jn nL (; Remaining: ) putinterval/nL nL 13 a def /lw 0.014 def/lb{gs X N 0 0 M D true charpath flattenpath pathbbox/uy x/ux x/ly x/lx x gs ux lx s 2 d lw a uy ly s 2 d lw a S N -1 -1 M 1 -1 L 1 1 L -1 1 L closepath 1 setgray fill gr ux lx a -2 d uy ly a -2 d M show gr}b/B{gs X R 1 S N 0 0 3 -1 r -90 90 arc C setmatrix L L bondPats e 1 s get/P x fB gr}b/sb{gs 2 copy X 3 -1 r e s 3 1 r s 2 copy atan R D m e D m a sqrt bondLWid S /iCg x /iCb x /iCr x /jCg x /jCb x /jCr x D 1 s 0 e X 1 setlinewidth N{0 0 M jCr jCb jCg RGB .5 0 L stroke .5 0 M 1 0 L iCr iCb iCg RGB stroke 0 -2 X}repeat gr}b /sc{/n x/maxZ x/minZ x/maxY x/minY x/maxX x/minX x currentpoint/uy x/ux x/ly x/lx x ux ly X lx ux s maxX minX s lw a d ly uy s maxY minY s lw a d 1 index 1 index gt{e p D maxX minX s lw a m lx ux s s -2 d 0}{p D maxY minY s lw a m ly uy s s 2 d 0 e}ifelse X D neg S lw 2 d minX s lw 2 d minY s X /C C currentmatrix def lw setlinewidth N}b /F{closepath gs P fill gr stroke}b 0.4000/Helvetica findfont exch scalefont setfont 0.0439/bondLWid x -4.0771 3.7976 -3.2726 3.7355 -1.8804 2.1378 42 sc 1 0.449 0.449 0.449 0.058 0.943 1.000 0.3202 -0.7637 -0.2585 -0.4834 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 2.5651 -0.8817 2.9687 -0.2279 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 3.7976 0.3877 2.9687 -0.2279 sb 1 1.000 0.161 0.161 0.058 0.943 1.000 -2.5649 -0.1581 -3.0872 -0.8127 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -0.9984 0.3111 -0.2585 -0.4834 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -1.0754 -2.4874 -0.9660 -1.7053 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 2.9687 -0.2279 1.8858 0.6624 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 2.9687 -0.2279 3.3682 -0.8666 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 2.9079 2.4310 2.0011 1.9949 sb 1 0.449 0.449 0.449 1.000 0.161 0.161 -3.0872 -0.8127 -2.3353 -1.2827 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.2585 -0.4834 -0.9660 -1.7053 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.2585 -0.4834 0.6828 -0.0076 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 0.7838 3.7355 0.9581 2.9486 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -0.8490 1.9662 -0.3532 2.2272 sb 2 0.449 0.449 0.449 0.449 0.449 0.449 2.0011 1.9949 1.8858 0.6624 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 2.0011 1.9949 0.9581 2.9486 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.8858 0.6624 0.6828 -0.0076 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.9660 -1.7053 -2.3353 -1.2827 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.9660 -1.7053 -0.1065 -2.2256 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.9581 2.9486 -0.3532 2.2272 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 0.9581 2.9486 1.3191 3.4271 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -3.1939 -3.2726 -3.0712 -2.4631 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -2.3353 -1.2827 -3.0712 -2.4631 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -2.3353 -1.2827 -2.1916 -0.1500 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.6828 -0.0076 1.0544 -1.2531 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.6828 -0.0076 -0.0608 0.9568 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.3532 2.2272 -0.0608 0.9568 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -0.3532 2.2272 -1.0223 2.8867 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 0.2794 -3.2408 -0.1065 -2.2256 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 1.9896 -1.6997 1.0544 -1.2531 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -1.9860 0.0456 -1.3633 0.3152 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -1.6385 0.6997 -2.1916 -0.1500 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -3.0712 -2.4631 -4.0771 -2.1403 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -3.0712 -2.4631 -2.4956 -2.8585 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.1065 -2.2256 1.0544 -1.2531 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -0.1065 -2.2256 -0.7086 -2.2646 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 1.0544 -1.2531 1.1871 -0.9995 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.0608 0.9568 -1.3633 0.3152 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -0.0608 0.9568 0.5700 1.1986 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -2.1916 -0.1500 -3.1965 0.2051 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -2.1916 -0.1500 -1.6306 -0.5048 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -1.3633 0.3152 -1.1460 -0.6070 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -1.3633 0.3152 -1.9317 1.0242 sb end +|'\xT*#(y   + H+x4++l   U U] p Z [ P { "8+ !, [f-.r!_/W#=4 $5 $6 x#=7P T? T@ AgBPgCl D KN P R<BUBVW UX< UYXZH 7l!acdmnHYo{|q}~q!kq_ZJZ 88K K< v*r,r-,**/S-(:-0l`*b,(- !},(#*b#)~!}.!}- $'!}- k/"          01E23<8 :9= ;FGHIJL O! Q"S#$[$%\%&]&'^'(_#(`()p&*b$,e)-q-.r./s(/t0112233445055637?C196::;;<5<=>>??@@AAB=B28@DBE>FIMGHHIIJJKKLGLJNLOHPMQTXRSSTTUUVVWRWUYWZS[X\%+ CH3 CH3 OHCH3CH3O CH3!COOEt"CH3)O*CH3+COOEt,CH3/O6O7CH38CH2OH9CH3<ODCH3EOFCH3NCH3OOPCH3Q CH(COOEt)2YCH3ZO[CH3\CH2-COOH `  !  D `  "0  `  g# \ h `  =$P P@  ` %P@ `  y(D  4 ` S)0 `  y*` x ` R >H  ` M  ` ?!{u!#( ` gfLx!\ ` >g@ ` h ` byiZ4 ` !jT4 D  ` ! k! (!  ` vT D ` bwZV ` #qxxh ` ]zx ` "x,h ` --<.,X ` ('(R ` -2-< p.,`.   00 08 ` -e$-,$@-% ` (!'V!4( ! ` -d,- ` 0D"~/"0'L m  0$0 X epi-Hinesol. .   (.P. DesLongchamps Can. J. Chem., (1980), 2460.6  `Dt '06This is an example of a compound of the spirane class. 8|\t Synthesis:  L< Ethylene glycol  LhLp Tosic acid  P#$&pLiAlH4   D  HCl  $$(1W1. Ketal formation and use as protecting group. 2. Isomerization with enone systems. 3. Lithium aluminum hydride, structure, reactivity, reaction conditions 4. Deprotection and mechanism  + *l+ D 1. Na/ EtOH F -0,`0-P (2. Diethylmalonate  *\*p* HCl, reflux - 215"$@5. Formation of the malonate anion 6. Malonic ester synthesis 7. !,4- additions, Michael Reactions, examination of HOMO-LUMO interactions 8. Hydrolysis and decarboxylation of malonic esters HelveticaGenevai   CHMD GrphbjdCHMD epi-Hinesol-2dCHMDHH(FG(HH(d'`CH3D_CGrphbj  HHdjCD3DDPRFd  Dj)$zX dCH3DPY-0symbCCCXCXCCCCCCXCCOCCOOCOOCHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXLpLpcart(Տ)ӥ(Ksz|XS ?u 8;q[#NPnCyB̻pbPY5J&'iUd hRe|b F߶ԃ=i2DUvˉ; Isg-+; 9M9͑<&PҸA_C >|oOdjCX@lIJ0k5 /J/D@y'Oh ewbond (    #  !        "  +,*)&' $ %  o p currentpoint !pQ" sss#Q"tsss#Q"Bsss#)()(",sss#)()(",sss#Q"Uxsss#"Q#sss"#"EQ#sss"E#Q"usss## Q# sss"w#Q"~sss#Q"Msss#Q"sss#Q"sss#"4 # "4)()(#sss"4#"  )()(# sss" Q#sss"c#"c#"c#"{#"{ # "{Q#sss"LQ#sss"J # "J#"JQ#sss"c # Q"" sss# " # "# "4Q#)()("sss#)()("sss#")()(#sss"#" )()(# sss" )()(# sss"gQ#ce UUUU")()(##ce#Q "qsss#)()(" sss# #Q#sss"Q#/dict3D 110 dict def dict3D begin % Copyright 1986-92 Cambridge Scientific Computing, Inc. /b{bind def}bind def/l{load def}b/X/translate l/R/rotate l/S/scale l/N/newpath l/gs/gsave l/gr/grestore l/e/exch l/r/roll l/p/pop l/s/sub l/d/div l/a/add l/m/mul l/D/dup l/L/lineto l/M/moveto l/A/arc l /C matrix def/E{X R 1 S 0 0 5 2 r arc C setmatrix}b/x{e def}b/G{64. d setgray fill}b /RGB{setrgbcolor}b /fB{closepath gs P fill gr stroke}b/pS 8 string def/pF 4.5 0 C defaultmatrix dtransform D 0 ne{e}if p D 9. d round d def/pA 1 0 C currentmatrix dtransform e atan def/pt{pS copy p pF pA{1 a 4 m cvi pS e get e 1 a 4 m cvi 7 s bitshift 1 and}setscreen 0 pS{8{D 1 and 3 -1 r a e -1 bitshift}repeat p}forall -64. d 1 a setgray}b/jn 80 string def/nL statusdict/jobname get jn copy length def jn nL (; Remaining: ) putinterval/nL nL 13 a def /lw 0.014 def/lb{gs X N 0 0 M D true charpath flattenpath pathbbox/uy x/ux x/ly x/lx x gs ux lx s 2 d lw a uy ly s 2 d lw a S N -1 -1 M 1 -1 L 1 1 L -1 1 L closepath 1 setgray fill gr ux lx a -2 d uy ly a -2 d M show gr}b/B{gs X R 1 S N 0 0 3 -1 r -90 90 arc C setmatrix L L bondPats e 1 s get/P x fB gr}b/sb{gs 2 copy X 3 -1 r e s 3 1 r s 2 copy atan R D m e D m a sqrt bondLWid S /iCg x /iCb x /iCr x /jCg x /jCb x /jCr x D 1 s 0 e X 1 setlinewidth N{0 0 M jCr jCb jCg RGB .5 0 L stroke .5 0 M 1 0 L iCr iCb iCg RGB stroke 0 -2 X}repeat gr}b /sc{/n x/maxZ x/minZ x/maxY x/minY x/maxX x/minX x currentpoint/uy x/ux x/ly x/lx x ux ly X lx ux s maxX minX s lw a d ly uy s maxY minY s lw a d 1 index 1 index gt{e p D maxX minX s lw a m lx ux s s -2 d 0}{p D maxY minY s lw a m ly uy s s 2 d 0 e}ifelse X D neg S lw 2 d minX s lw 2 d minY s X /C C currentmatrix def lw setlinewidth N}b /F{closepath gs P fill gr stroke}b 0.4286/Helvetica findfont exch scalefont setfont 0.0439/bondLWid x -2.2794 3.2800 -5.0356 5.0993 -3.2246 3.1462 45 sc 1 0.449 0.449 0.449 0.058 0.943 1.000 1.2973 4.4031 0.8988 3.8559 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 1.5567 -1.3074 2.0456 -1.4509 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -0.4923 1.3570 -1.2794 1.2203 sb 1 0.449 0.449 0.449 1.000 0.161 0.161 1.3119 2.5227 0.8988 3.8559 sb 1 0.449 0.449 0.449 1.000 0.161 0.161 1.3119 2.5227 1.5702 2.1037 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -1.9310 0.3666 -1.2794 1.2203 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 0.8988 3.8559 -0.1984 3.8338 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.8988 3.8559 1.5955 4.3202 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -1.2794 1.2203 -1.8993 2.1430 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -1.2794 1.2203 -0.6364 0.9454 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 3.1465 -1.3403 2.0456 -1.4509 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 2.0456 -1.4509 1.7937 -2.4644 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 2.0456 -1.4509 1.5406 -0.4103 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -1.0387 -1.8165 -0.7004 -1.6691 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 3.2800 0.8010 2.3435 0.8381 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 0.8378 -3.0858 0.3097 -2.7497 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 2.3419 5.0993 1.5955 4.3202 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.5702 2.1037 2.3435 0.8381 sb 1 1.000 0.161 0.161 0.449 0.449 0.449 1.5702 2.1037 2.3213 3.1953 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.5702 2.1037 0.2458 2.1112 sb 1 1.000 0.161 0.161 0.449 0.449 0.449 1.5955 4.3202 2.3213 3.1953 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 1.5955 4.3202 0.8462 4.5300 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.5406 -0.4103 2.3435 0.8381 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.5406 -0.4103 0.0726 -0.3816 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.5406 -0.4103 1.0639 -0.6236 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.7004 -1.6691 0.0726 -0.3816 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.7004 -1.6691 0.3097 -2.7497 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -0.7004 -1.6691 -1.5235 -1.6658 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 2.3435 0.8381 2.6513 0.8736 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.6364 0.9454 0.0726 -0.3816 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.6364 0.9454 0.2458 2.1112 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -0.6364 0.9454 -1.5210 0.9122 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.0726 -0.3816 1.0639 -0.6236 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -0.2905 3.0646 0.2458 2.1112 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.3097 -2.7497 -0.3710 -3.8487 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.3097 -2.7497 1.2666 -2.0563 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 0.2458 2.1112 0.4422 2.0797 sb 2 0.449 0.449 0.449 1.000 0.161 0.161 -0.0722 -5.0149 -0.3710 -3.8487 sb 1 1.000 0.161 0.161 0.449 0.449 0.449 -0.3710 -3.8487 -0.8644 -3.2873 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.2666 -2.0563 1.0639 -0.6236 sb 2 1.000 0.161 0.161 0.449 0.449 0.449 1.2666 -2.0563 2.2982 -2.5669 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 1.0639 -0.6236 1.2492 0.0607 sb 1 1.000 0.161 0.161 1.000 0.611 0.779 -1.2858 -2.9246 -0.8644 -3.2873 sb 1 1.000 0.611 0.779 1.000 0.161 0.161 -0.8644 -3.2873 -0.3566 -3.1393 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -2.2794 -4.7331 -1.5126 -4.2622 sb 1 0.449 0.449 0.449 1.000 0.161 0.161 -0.8644 -3.2873 -1.5126 -4.2622 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -1.5126 -4.2622 -0.7491 -5.0356 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -1.5126 -4.2622 -1.8141 -3.7684 sb end count     currentpoint 192837465 ! currentpoint   " save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1993, Cambridge Scientific Computing, Inc. userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub L/T/true L/tr/transform L/xl/translate L/xc/exec L/A R/N R/St R/X R/Y R/aL R/bL R/bS R/bd R/bs R/cX R/cY R/ch R/co R/fB R/fI R/fS R/fZ R/fl R/ft R/iX R/iY R/idx R/lh R/llx R/lly R/lp R/nH R/nSq R/newdict R/ps R/rad R/rev R/sL R/sba R/sbl R/sbs R/sn R/spa R/tB R/typ R/urx R/ury R/w R/wF R/xX R/xY R/rBg R/gBg R/bBg R/gry R/rDst R/gDst R/bDst R/sf 20 d/cW 20 d/lW 20 d/bW 75 d/wF 1.5 d/aF 11.875 d/aR 0.263 d/aA 50 d/hS 54 d/pA 32 d/sh F d/S{sf m}b/dL{[hS] 0 setdash}b/o{1 ix}b/rot{3 -1 r}b/x{e d}b/CMT mt d/TM mt d/SM{CMT sm}b/XY{X D m Y D m a sq}b/s1 1 string d/fp{T charpath flattenpath}b/p{tr ru 0.25 a e ru 0.25 a e itransform}b/C{65536. dv rot 65536. dv rot 65536. dv rot setrgbcolor}b/sg{D currenthsbcolor P rot sethsbcolor currenthsbcolor e P e P o s D m .001 gt{setgray}{P}ie}b/sBg{65535 dv/bBg x 65535 dv/gBg x 65535 dv/rBg x}b/sRmp{currentrgbcolor bBg e s/bDst x gBg e s/gDst x rBg e s/rDst x}b/N 0 d/db{array/bs x/N 0 d}b/B{bs N rot put/N N 1 a d}b/SpA{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie aR aL m n D aL a 0 p M 0 o n aA n aA arc cp f gr}b/SpH{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie 0 cw 2 dv xl aR aL m n D aL a 0 p M 0 o n aA n 0 arc cp f gr}b/Sp{/St x 0.316/aR x gs aF lW m 0.8 m St 4 and 0 ne{bW m lW dv bW sl}if/aL x St 8 and 0 ne{8 ix 8 ix 3 ix 3 ix SpA}if St 16 and 0 ne{2 ix 6 m 1 a D ix e D ix e D ix e D ix e P SpA}if St 32 and 0 ne{8 ix 8 ix 3 ix 3 ix SpH}if St 64 and 0 ne{2 ix 6 m 1 a D ix e D ix e D ix e D ix e P SpH}if St 2 and 0 ne{St 4 and 0 ne{[hS bW m lW dv] 0 setdash}{dL}ie}if np M{cv}rp St 128 and 0 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M 0 -2 l Ast}{5 Aos 1 -1 M -1 -1 l 1 1 M -1 1 l 0 2 M 0 -2 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{4.5 Aos 1 0 M -1 0 l Ast}{gRc}{gRr}{Rc blf}{Rr blf}{Ac blf}{Ov blf}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro DLB -1 -1 sc DLB blf}{Asc gs -1 -1 sc ZLB blf gr gs 3.6 12 sc Cr whf gr ZLB blf}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc Cr blf gr ZLB whf}{Asc LB gs whf gr np -0.4 -0.4 sc LB blf}{Asc LB gs f gr gs SM st gr np -0.4 -0.4 sc LB whf}{Asc LB blf}{Asc LB gs f gr gs SM st gr np -1 -1 sc LB whf}{Ac whf}{OrA gAc}{Ac blf}{Ov whf}{OrA 1 .4 sc gOv}{Ov blf}}e 39 s g xc gr}ie}b/DS{np p M p l st}b/DD{gs dL DS gr}b/DB{gs 12 OB bW sl np 0 0 p M 0 p l st gr}b/ap{e 3 ix a e 2 ix a}b/PT{D 2 4 gi al P OP D 1 sc o length 6 gt{P 6 g}{e P 8 dv}ie D lW 2 m lt{P lW 2 m}if 0 e p 0 0 p 3 -1 r s 3 1 r e s e 0 0 p M 1 0 p l 0 0 p ap M 1 0 p ap l e n e n 0 0 p ap M 1 0 p ap l P P}b f/DT{gs np PT SM st gr}b/NH{lW s D hS dv ru cvi D 0 eq{P 1}if/nH x D hS nH m s D 0 lt{P .1 s nH dv}{nH 2 a dv D 0 xl 2 m s nH dv}ie}b/Bd{D type/arraytype ne{bs e g}if{{P}{{{DS}{DD}{gs 12 OB np bW 2 dv/bd x lW 2 dv e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b q4l<z8z<l8m4l8z"7l"B"M"Mq&BNBCDNNMB",q",C,,BCB,"."  q ,! ,,!","C q"BKJKDCBJ"D"E"H"J"L"cq"NdddNNNd"q"""""nqeomoeemq/H7V3V7H3I/H3V"2H"E~"P"E "B "/q"/E//EEE/"# q"#.$##..$"# "Mq"ENLNFEEL"F{"Hx"Ju"Lr"Oo"fq"QgggQQQg"pqhqpqhhp"" q"###"""" qssts"s"""q&" "q"" q"" " q"""""""q""q""q"q"q" "}"" " "q"" q"" "q""z"w"t"q"n"q""q" q"xxyx"^"^"m"x qcqqcdcq"c"s0qm&t1r1t1n&m&r1"i> qi1t?i?j?t1r1i?"mG"j<"^? end %%EndProcSet 40 60 28 20 60 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 517 707 10 4 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C 2430 1110 350 1110 2 Ar np 3244 1326 M 3216 1342 l 3216 872 l 3244 888 l cp f np 3623 1545 M 3623 1561 l 3609 1569 l 3216 1342 l 3244 1326 l cp f np 4003 1326 M 4017 1334 l 4017 1350 l 3637 1569 l 3623 1561 l 3623 1545 l cp f np 4003 888 M 4031 872 l 4031 1326 l 4017 1334 l 4003 1326 l cp f np 3921 928 M 3949 928 l 3949 1287 l 3921 1287 l cp f np 3623 668 M 3623 636 l 4031 872 l 4003 888 l cp f np 3623 636 M 3623 668 l 3244 888 l 3216 872 l cp f np 4295 1478 M 4281 1502 l 4017 1350 l 4017 1334 l 4031 1326 l cp f[1 4 3179 1363 2922 1511 ]Bd np 3637 2008 M 3609 2022 l 3609 1569 l 3623 1561 l 3637 1569 l cp f np 3568 330 M 3596 330 l 3596 675 l 3568 675 l cp f np 3650 330 M 3678 330 l 3678 675 l 3650 675 l cp f np 3866 2189 M 3848 2211 l 3609 2022 l 3637 2008 l cp f 6830 1010 4690 1010 2 Ar np 7664 1376 M 7636 1392 l 7636 922 l 7664 938 l cp f np 8043 1595 M 8043 1611 l 8029 1619 l 7636 1392 l 7664 1376 l cp f np 8423 1376 M 8437 1384 l 8437 1400 l 8057 1619 l 8043 1611 l 8043 1595 l cp f np 8348 1325 M 8362 1349 l 8050 1528 l 8036 1504 l cp f np 8423 938 M 8451 922 l 8451 1376 l 8437 1384 l 8423 1376 l cp f np 8043 718 M 8043 702 l 8070 701 l 8451 922 l 8423 938 l cp f np 8018 701 M 8043 702 l 8043 718 l 7664 938 l 7636 922 l cp f np 8711 1526 M 8697 1550 l 8437 1400 l 8437 1384 l 8451 1376 l cp f[1 4 7600 1413 7347 1559 ]Bd np 8057 2058 M 8029 2072 l 8029 1619 l 8043 1611 l 8057 1619 l cp f np 8291 2242 M 8273 2264 l 8029 2072 l 8057 2058 l cp f np 8281 521 M 8297 545 l 8070 701 l 8043 702 l 8042 685 l cp f np 8278 22 M 8298 -6 l 8388 295 l 8362 303 l cp f np 7741 312 M 7715 302 l 7823 -6 l 7843 22 l cp f np 7783 533 M 7799 511 l 8042 685 l 8043 702 l 8018 701 l cp f 2570 3370 330 3370 2 Ar np 3144 3926 M 3116 3942 l 3116 3472 l 3144 3488 l cp f np 3523 4145 M 3523 4161 l 3509 4169 l 3116 3942 l 3144 3926 l cp f np 3903 3926 M 3917 3934 l 3917 3950 l 3537 4169 l 3523 4161 l 3523 4145 l cp f np 3828 3875 M 3842 3899 l 3530 4078 l 3516 4054 l cp f np 3903 3488 M 3931 3472 l 3931 3926 l 3917 3934 l 3903 3926 l cp f np 3523 3268 M 3523 3252 l 3549 3251 l 3931 3472 l 3903 3488 l cp f np 3498 3251 M 3523 3252 l 3523 3268 l 3144 3488 l 3116 3472 l cp f np 4195 4078 M 4181 4102 l 3917 3950 l 3917 3934 l 3931 3926 l cp f[1 4 3079 3963 2822 4111 ]Bd np 3537 4608 M 3509 4622 l 3509 4169 l 3523 4161 l 3537 4169 l cp f np 3766 4789 M 3748 4811 l 3509 4622 l 3537 4608 l cp f np 3761 3070 M 3777 3094 l 3549 3251 l 3523 3252 l 3522 3235 l cp f np 3758 2572 M 3778 2544 l 3870 2855 l 3844 2863 l cp f np 3323 2572 M 3303 2544 l 3778 2544 l 3758 2572 l cp f np 3218 2871 M 3192 2861 l 3303 2544 l 3323 2572 l cp f np 3263 3083 M 3279 3061 l 3522 3235 l 3523 3252 l 3498 3251 l cp f np 2524 8376 M 2496 8392 l 2496 7922 l 2524 7938 l cp f np 2903 8595 M 2903 8611 l 2889 8619 l 2496 8392 l 2524 8376 l cp f np 3283 8376 M 3297 8384 l 3297 8400 l 2917 8619 l 2903 8611 l 2903 8595 l cp f np 3208 8325 M 3222 8349 l 2910 8528 l 2896 8504 l cp f np 3283 7938 M 3311 7922 l 3311 8376 l 3297 8384 l 3283 8376 l cp f np 2903 7718 M 2903 7702 l 2930 7701 l 3311 7922 l 3283 7938 l cp f np 2878 7701 M 2903 7702 l 2903 7718 l 2524 7938 l 2496 7922 l cp f np 3571 8526 M 3557 8550 l 3297 8400 l 3297 8384 l 3311 8376 l cp f[1 4 2460 8413 2207 8559 ]Bd np 2917 9058 M 2889 9072 l 2889 8619 l 2903 8611 l 2917 8619 l cp f np 3274 9339 M 3246 9353 l 2889 9072 l 2917 9058 l cp f np 3141 7521 M 3157 7545 l 2930 7701 l 2903 7702 l 2902 7685 l cp f np 3138 7022 M 3158 6994 l 3248 7295 l 3222 7303 l cp f np 2703 7022 M 2683 6994 l 3158 6994 l 3138 7022 l cp f np 2601 7312 M 2575 7302 l 2683 6994 l 2703 7022 l cp f np 2643 7533 M 2659 7511 l 2902 7685 l 2903 7702 l 2878 7701 l cp f 2250 7870 290 7870 2 Ar np 979 7396 M 981 7430 l 755 7320 l 767 7294 l cp f np 1254 7210 M 1256 7244 l 981 7430 l 979 7396 l cp f np 1427 7295 M 1415 7321 l 1256 7244 l 1254 7210 l cp f np 1191 7016 M 1219 7014 l 1236 7248 l 1208 7250 l cp f np 1261 "r3 "r0 qr/}1}1}/r/r0}1"q"q""qqIWWIJIW"I"v""q&"q""} q"}~}}~"} "" "" q&#q&"""""""s"p"m"j"g""""""| q"s}su}}|s"Z qYh[Yhh["ZqY[[YY[["gzqYyh~h{hyY~[~h{"s} "q"qqxyuyxuyqxu"tx"xqcyyyccy"q"zzz"q&yyz{y"c"X "X q"XcXXXccX" " q"    " q"     "z q&y   {zy "q&  """""""{"|"~""""w"u"s"q"o"N "4"4"C"N q"MXOMWXXO" "q"q" d7010 M 1289 7008 l 1305 7243 l 1277 7245 l cp f np 1043 7605 M 1015 7607 l 999 7392 l 1027 7390 l cp f np 973 7611 M 945 7613 l 930 7397 l 958 7395 l cp f np 3274 9793 M 3246 9807 l 3246 9353 l 3274 9339 l cp f np 3512 9980 M 3494 10002 l 3246 9807 l 3274 9793 l cp f np 2999 9988 M 2987 9962 l 3290 9815 l 3302 9841 l cp f np 2963 9914 M 2951 9888 l 3254 9742 l 3266 9768 l cp f 6850 7890 4350 7890 2 Ar np 7504 8296 M 7476 8312 l 7476 7842 l 7504 7858 l cp f np 7883 8515 M 7883 8531 l 7880 8545 l 7476 8312 l 7504 8296 l cp f np 8263 8296 M 8277 8304 l 8277 8320 l 7940 8514 l 7883 8531 l 7883 8515 l cp f np 8263 7858 M 8291 7842 l 8291 8295 l 8277 8304 l 8263 8296 l cp f np 7883 7638 M 7883 7622 l 7908 7620 l 8291 7842 l 8263 7858 l cp f np 7858 7621 M 7883 7622 l 7883 7638 l 7504 7858 l 7476 7842 l cp f np 8308 9175 M 8312 9207 l 7900 8996 l 7912 8972 l cp f np 8677 8937 M 8705 8953 l 8312 9207 l 8308 9175 l cp f np 8656 8507 M 8669 8492 l 8683 8483 l 8705 8953 l 8677 8937 l cp f np 8683 8483 M 8669 8492 l 8612 8481 l 8277 8320 l 8277 8304 l 8291 8295 l cp f np 8612 8481 M 8669 8492 l 8656 8507 l 7880 8545 l 7883 8531 l 7940 8514 l cp f[1 3 7885 8587 7904 8928 ]Bd [1 4 7440 8333 7187 8479 ]Bd [1 4 8332 8275 8553 8156 ]Bd np 8122 7429 M 8138 7451 l 7908 7620 l 7883 7622 l 7883 7605 l cp f np 8094 6936 M 8114 6908 l 8212 7201 l 8186 7209 l cp f np 7661 6936 M 7641 6908 l 8114 6908 l 8094 6936 l cp f np 7574 7208 M 7548 7200 l 7641 6908 l 7661 6936 l cp f np 7623 7449 M 7639 7427 l 7883 7605 l 7883 7622 l 7858 7621 l cp f np 8990 9037 M 8978 9061 l 8683 8910 l 8695 8886 l cp f np 8952 9111 M 8940 9135 l 8645 8983 l 8657 8959 l cp f 2670 12570 350 12570 2 Ar np 4134 12666 M 4106 12682 l 4106 12212 l 4134 12228 l cp f np 4513 12885 M 4513 12901 l 4510 12915 l 4106 12682 l 4134 12666 l cp f np 4893 12666 M 4907 12674 l 4907 12690 l 4570 12884 l 4513 12901 l 4513 12885 l cp f np 4893 12228 M 4921 12212 l 4921 12665 l 4907 12674 l 4893 12666 l cp f np 4513 12008 M 4513 11992 l 4538 11990 l 4921 12212 l 4893 12228 l cp f np 4488 11990 M 4513 11992 l 4513 12008 l 4134 12228 l 4106 12212 l cp f np 4938 13545 M 4940 13561 l 4926 13569 l 4530 13366 l 4542 13342 l cp f np 5307 13307 M 5335 13323 l 4955 13568 l 4940 13561 l 4938 13545 l cp f np 5286 12877 M 5299 12862 l 5313 12853 l 5335 13323 l 5307 13307 l cp f np 5313 12853 M 5299 12862 l 5242 12851 l 4907 12690 l 4907 12674 l 4921 12665 l cp f np 5242 12851 M 5299 12862 l 5286 12877 l 4510 12915 l 4513 12901 l 4570 12884 l cp f[1 3 4515 12957 4534 13298 ]Bd [1 4 4068 12704 3805 12855 ]Bd [1 4 4961 12645 5179 12527 ]Bd np 4741 11807 M 4757 11829 l 4538 11990 l 4513 11992 l 4513 11975 l cp f np 4724 11306 M 4744 11278 l 4844 11577 l 4818 11585 l cp f np 4291 11306 M 4271 11278 l 4744 11278 l 4724 11306 l cp f np 4200 11591 M 4174 11583 l 4271 11278 l 4291 11306 l cp f np 4242 11811 M 4258 11789 l 4513 11975 l 4513 11992 l 4488 11991 l cp f np 5630 13412 M 5618 13436 l 5313 13280 l 5325 13256 l cp f np 5592 13486 M 5580 13510 l 5275 13353 l 5287 13329 l cp f np 5001 13856 M 4911 13860 l 4926 13569 l 4940 13561 l 4955 13568 l cp f gr count origstk sub{P}rp end chemsave restore ,  Helvetica .+SCH +3 (SzH *+ 3 +(SC(O+iCH +2 `(w-COOMe(UCH +3 (UWH *+ 3 +(UeC+:%CH +2 `(z-COOMe(O({O(CH +3 (uH *+ 3 +(C+:$CH +2 `(-COOH(O(O(CH +3 (VH *+ 3 +(dC(yO(yzO(pCl+0Cl(]9O(-O+uCHN +2 (O(OH *+ 3 +(]C(CH +3 (tO(tsO(*'CH +2 `(*=N + 2 (O((Ethylene glycol+ Tosic acid()KOH(# hydrolysis("O9. Diazomethane. Preparation, handling, and mechanism for esterification. * _10. Discussion of the functional group problems and the need for the many protection and * &deprotections steps in this approach. * K11. What about yields? How do the number of steps influence total yields?(H *+ 3 +(C(sCH +3 (OO(OO( Ph-H, heat(Cu(O(+ isomer(1.*2. CH ,+2 -(;N `+2 (COOMe( '12. Methods for making acid chlorides * 13. Diazoketone formation * ?14. Introduction to similar ideas of Arndt-Eistert chemistry * 15. Carbenes from diazoketones+ 0Dimethylcarbonate+NaH(13. Methodology for adding *  carbomethoxy groups. * 14. Sodium hydride as based2"CHMDSTRG   x(<<|'t6%:|_C _CCH3D_CGrphbj HHUdjCD3DDPRFd  Dj)$zX dCH3DPY-0symbCCCXCXCCCCCCXCCOCCOOCOOCHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXHXLpLpcart(Տ)ӥ(Ksz|XS ?u 8;q[#NPnCyB̻pbPY5J&'iUd hRe|b F߶ԃ=i2DUvˉ; Isg-+; 9M9͑<&PҸA_C >|oOdjCX@lIJ0k5 /J/D@y'Oh ewbond (    #  !        "  +,*)&' $ %  _C `B currentpoint ! `Q"6sss#Q"sss#Q"sss#)()("jsss#)()("jsss#Q"l sss# "EQ#sss"E # "~Q#sss"~ # Q"sss##Q#sss"#Q"sss#Q"sss#Q"sss#Q"" sss# "v # "v )()(# sss"v#"8 )()(# sss"8Q#sss" # "#"#" # "#"Q#sss"Q#sss" # " # "Q#sss"#Q"[ sss#"#" # "vQ#)()("<sss#)()(">sss#")()(#sss"#")()(#sss")()(#sss"Q#ce UUUU"~)()(##ce#Q "6b sss# )()(" sss## Q# sss"(xQ#/dict3D 110 dict def dict3D begin % Copyright 1986-92 Cambridge Scientific Computing, Inc. /b{bind def}bind def/l{load def}b/X/translate l/R/rotate l/S/scale l/N/newpath l/gs/gsave l/gr/grestore l/e/exch l/r/roll l/p/pop l/s/sub l/d/div l/a/add l/m/mul l/D/dup l/L/lineto l/M/moveto l/A/arc l /C matrix def/E{X R 1 S 0 0 5 2 r arc C setmatrix}b/x{e def}b/G{64. d setgray fill}b /RGB{setrgbcolor}b /fB{closepath gs P fill gr stroke}b/pS 8 string def/pF 4.5 0 C defaultmatrix dtransform D 0 ne{e}if p D 9. d round d def/pA 1 0 C currentmatrix dtransform e atan def/pt{pS copy p pF pA{1 a 4 m cvi pS e get e 1 a 4 m cvi 7 s bitshift 1 and}setscreen 0 pS{8{D 1 and 3 -1 r a e -1 bitshift}repeat p}forall -64. d 1 a setgray}b/jn 80 string def/nL statusdict/jobname get jn copy length def jn nL (; Remaining: ) putinterval/nL nL 13 a def /lw 0.014 def/lb{gs X N 0 0 M D true charpath flattenpath pathbbox/uy x/ux x/ly x/lx x gs ux lx s 2 d lw a uy ly s 2 d lw a S N -1 -1 M 1 -1 L 1 1 L -1 1 L closepath 1 setgray fill gr ux lx a -2 d uy ly a -2 d M show gr}b/B{gs X R 1 S N 0 0 3 -1 r -90 90 arc C setmatrix L L bondPats e 1 s get/P x fB gr}b/sb{gs 2 copy X 3 -1 r e s 3 1 r s 2 copy atan R D m e D m a sqrt bondLWid S /iCg x /iCb x /iCr x /jCg x /jCb x /jCr x D 1 s 0 e X 1 setlinewidth N{0 0 M jCr jCb jCg RGB .5 0 L stroke .5 0 M 1 0 L iCr iCb iCg RGB stroke 0 -2 X}repeat gr}b /sc{/n x/maxZ x/minZ x/maxY x/minY x/maxX x/minX x currentpoint/uy x/ux x/ly x/lx x ux ly X lx ux s maxX minX s lw a d ly uy s maxY minY s lw a d 1 index 1 index gt{e p D maxX minX s lw a m lx ux s s -2 d 0}{p D maxY minY s lw a m ly uy s s 2 d 0 e}ifelse X D neg S lw 2 d minX s lw 2 d minY s X /C C currentmatrix def lw setlinewidth N}b /F{closepath gs P fill gr stroke}b 0.4286/Helvetica findfont exch scalefont setfont 0.0439/bondLWid x -2.2794 3.2800 -5.0356 5.0993 -3.2246 3.1462 45 sc 1 0.449 0.449 0.449 0.058 0.943 1.000 1.2973 4.4031 0.8988 3.8559 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 1.5567 -1.3074 2.0456 -1.4509 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -0.4923 1.3570 -1.2794 1.2203 sb 1 0.449 0.449 0.449 1.000 0.161 0.161 1.3119 2.5227 0.8988 3.8559 sb 1 0.449 0.449 0.449 1.000 0.161 0.161 1.3119 2.5227 1.5702 2.1037 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -1.9310 0.3666 -1.2794 1.2203 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 0.8988 3.8559 -0.1984 3.8338 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.8988 3.8559 1.5955 4.3202 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -1.2794 1.2203 -1.8993 2.1430 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -1.2794 1.2203 -0.6364 0.9454 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 3.1465 -1.3403 2.0456 -1.4509 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 2.0456 -1.4509 1.7937 -2.4644 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 2.0456 -1.4509 1.5406 -0.4103 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -1.0387 -1.8165 -0.7004 -1.6691 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 3.2800 0.8010 2.3435 0.8381 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 0.8378 -3.0858 0.3097 -2.7497 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 2.3419 5.0993 1.5955 4.3202 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.5702 2.1037 2.3435 0.8381 sb 1 1.000 0.161 0.161 0.449 0.449 0.449 1.5702 2.1037 2.3213 3.1953 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.5702 2.1037 0.2458 2.1112 sb 1 1.000 0.161 0.161 0.449 0.449 0.449 1.5955 4.3202 2.3213 3.1953 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 1.5955 4.3202 0.8462 4.5300 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.5406 -0.4103 2.3435 0.8381 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.5406 -0.4103 0.0726 -0.3816 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.5406 -0.4103 1.0639 -0.6236 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.7004 -1.6691 0.0726 -0.3816 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.7004 -1.6691 0.3097 -2.7497 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -0.7004 -1.6691 -1.5235 -1.6658 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 2.3435 0.8381 2.6513 0.8736 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.6364 0.9454 0.0726 -0.3816 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 -0.6364 0.9454 0.2458 2.1112 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -0.6364 0.9454 -1.5210 0.9122 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.0726 -0.3816 1.0639 -0.6236 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -0.2905 3.0646 0.2458 2.1112 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.3097 -2.7497 -0.3710 -3.8487 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 0.3097 -2.7497 1.2666 -2.0563 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 0.2458 2.1112 0.4422 2.0797 sb 2 0.449 0.449 0.449 1.000 0.161 0.161 -0.0722 -5.0149 -0.3710 -3.8487 sb 1 1.000 0.161 0.161 0.449 0.449 0.449 -0.3710 -3.8487 -0.8644 -3.2873 sb 1 0.449 0.449 0.449 0.449 0.449 0.449 1.2666 -2.0563 1.0639 -0.6236 sb 2 1.000 0.161 0.161 0.449 0.449 0.449 1.2666 -2.0563 2.2982 -2.5669 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 1.0639 -0.6236 1.2492 0.0607 sb 1 1.000 0.161 0.161 1.000 0.611 0.779 -1.2858 -2.9246 -0.8644 -3.2873 sb 1 1.000 0.611 0.779 1.000 0.161 0.161 -0.8644 -3.2873 -0.3566 -3.1393 sb 1 0.449 0.449 0.449 0.058 0.943 1.000 -2.2794 -4.7331 -1.5126 -4.2622 sb 1 0.449 0.449 0.449 1.000 0.161 0.161 -0.8644 -3.2873 -1.5126 -4.2622 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -1.5126 -4.2622 -0.7491 -5.0356 sb 1 0.058 0.943 1.000 0.449 0.449 0.449 -1.5126 -4.2622 -1.8141 -3.7684 sb end  L Lh\\  TA,  1 x1hf , 1,f11E1 ^ Au!^ " #u$u1A"+ 6@c- 3 j78 9 DDT DE7 FTWG WH I V7P C[6 R2X \ ] c^ g h! ai j k al#_ ax!us |!Ou$x zV V}V ~ [1&> 6'V*' -L fL!I f _ _## "!!"!!H! Be##/"1x"2[1x5/5.4 4V3242Z0-,,-;4g6m        2 % & '() *,: .4;<=>WJKLMNO Q!_"S#Y!$`$%a%&b&c)-y'(m()n)*o*+p+,q',r*.t,/(0v-1{/22334,4566778197:6;9<9=>??@@AABBC>C?HDEEFFGAG@D@GAICJJKKLLMCMFNOPPQQRRSSTOTPYUVVWWXRXQUQXRZT[[\\]]^T^W_V`CH3O CH3  CH2-COOMeCH3OCH3 CH2-COOMeO CH3!O"CH3#CH2-COOH&O.CH3/O0CH34O5Cl8Cl:O;O<CHN2=OHCH3ICH3JOMONOYCH3ZCH3[O^O_O`COOMe ` i `  d  ` h h  @ `n  H2P  ` "%"8# `  Z !B `  `  z v0 % `(  ?Zb ` }/  `  5 P  `  @ 8  ` pB `   C P    ` !U!H$"8 ` d se f . ` !T!H"8p ` d Z f N ` d ` fp$| ` @uB0 ` M ` ' w& ' ` '] & '_  ` ! @! ` !,! #( ` V  ` V  ` $#-#^#H$# ` 22 2 ` 0a0Hx18 ` .-h.o ` .-h. ` 5"4p5$ `V 7 6`$7l*n  `  ( 4  pCH2N2   XH(Ethylene glycol  8 Tosic acid m  D4 H D(KOH h `  hydrolysis  hh&O9. Diazomethane. Preparation, handling, and mechanism for esterification. 10. Discussion of the functional group problems and the need for the many protection and deprotections steps in this approach. 11. What about yields? How do the number of steps influence total yields? E $1.*  S `   D x2. CH2N2  tLCu   D l\ Ph-H, heat  %,%)+ isomer m )@(,L('B12. Methods for making acid chlorides 13. Diazoketone formation 14. Introduction to similar ideas of Arndt-Eistert chemistry 15. Carbenes from diazoketones  0 /X0H Dimethylcarbonate  2D1`X2NaHU  5 T4Xh7P p9U13. Methodology for adding carbomethoxy groups. 14. Sodium hydride as base Helveticapp])])] - -CHMD -GrphbjdCHMD epi-Hinesol-3dCHMDHH(FG(HH(d'`count      -currentpoint 192837465 ! currentpoint   -" save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1993, Cambridge Scientific Computing, Inc. userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub L/T/true L/tr/transform L/xl/translate L/xc/exec L/A R/N R/St R/X R/Y R/aL R/bL R/bS R/bd R/bs R/cX R/cY R/ch R/co 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lp neg o lp ac 0 Y 2 dv 0 Y lp ac 0 Y lp Y lp ac X lp s 0 p M X 0 X Y lp ac X Y 2 dv X lp a o lp ac X Y 2 dv X Y lp ac X Y X lp s Y lp ac SM st}{Y D 2 dv Y 180 pA s 180 pA a arc st np X Y s Y 2 dv Y pA D neg arcn st}{Rc SM st}{X lW 2 dv a lW -2 dv p M rO D rlineto X lW 2 dv a rO a Y lW 2 dv a rO a p l rO lW -2 dv a Y lW 2 dv a rO a p l lW -2 dv Y lW 2 dv a p l 0 Y p l X Y p l X 0 p l cp f 0 0 p M 0 Y p l X Y p l X 0 p l cp SM st}{Rr SM st}{rO Y p M rO rO xl 0 Y X Y rO ac X Y X 0 rO ac X 0 0 0 rO ac rO neg D xl X Y 0 Y rO ac cp f Rr st}{Ac st}{OrA gAc}{Ov st}{OrA 1 .4 sc gOv}{Asc LB whf}{Asc gLB}{Asc gs gLB gr -1 -1 sc LB whf}{Asc gs gLB gr -0.4 -0.4 sc LB whf}{Asc LB gs whf gr np -0.4 -0.4 sc gLB}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro gs gDLB gr -1 -1 sc gDLB}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc gOv gr ZLB whf}{Asc gs -1 -1 sc gZLB gr gs 3.6 12 sc Cr whf gr gZLB}{0 0 p M X Y p l SM st}{bW sl 0 0 p M X Y p l SM st}{dL 0 0 p M X Y p l SM st}{OrA 1 16 dv D sc 0 -1 p M 0 0 1 0 1 ac 8 0 8 1 1 ac 8 0 16 0 1 ac 16 0 16 -1 1 ac SM st}{XY D 0 0 dt X Y dt}{XY 2 dv X Y dt}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l 2 0 M 0 0 2 0 360 arc Ast}{4.5 Aos 1 0 M -1 0 l 2 0 M 0 0 2 0 360 arc Ast}{2.25 Ath}{1.5 Ath}{1 Ath}{2.25 Aeq}{1.5 Aeq}{1 Aeq}{OrA 1 16 dv D sc 0 -1 p M 0 0 p l 16 0 p l 16 -1 p l SM st}{5 Aos 1 -1 M -1 -1 l 0 2 M 0 -2 l Ast}{5 Aos 1 -1 M -1 -1 l 1 1 M -1 1 l 0 2 M 0 -2 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{4.5 Aos 1 0 M -1 0 l Ast}{gRc}{gRr}{Rc blf}{Rr blf}{Ac blf}{Ov blf}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro DLB -1 -1 sc DLB blf}{Asc gs -1 -1 sc ZLB blf gr gs 3.6 12 sc Cr whf gr ZLB blf}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc Cr blf gr ZLB whf}{Asc LB gs whf gr np -0.4 -0.4 sc LB blf}{Asc LB gs f gr gs SM st gr np -0.4 -0.4 sc LB whf}{Asc LB blf}{Asc LB gs f gr gs SM st gr np -1 -1 sc LB whf}{Ac whf}{OrA gAc}{Ac blf}{Ov whf}{OrA 1 .4 sc gOv}{Ov blf}}e 39 s g xc gr}ie}b/DS{np p M p l st}b/DD{gs dL DS gr}b/DB{gs 12 OB bW sl np 0 0 p M 0 p l st gr}b/ap{e 3 ix a e 2 ix a}b/PT{D 2 4 gi al P OP D 1 sc o length 6 gt{P 6 g}{e P 8 dv}ie D lW 2 m lt{P lW 2 m}if 0 e p 0 0 p 3 -1 r s 3 1 r e s e 0 0 p M 1 0 p l 0 0 p ap M 1 0 p ap l e n e n 0 0 p ap M 1 0 p ap l P P}b f/DT{gs np PT SM st gr}b/NH{lW s D hS dv ru cvi D 0 eq{P 1}if/nH x D hS nH m s D 0 lt{P .1 s nH dv}{nH 2 a dv D 0 xl 2 m s nH dv}ie}b/Bd{D type/arraytype ne{bs e g}if{{P}{{{DS}{DD}{gs 12 OB np bW 2 dv/bd x lW 2 dv e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b "Mz"X"Xq&MXMMNXXXM"7q"7M77MMM7"+ q"+6,++66,"+ "y"m "V"M q&MWVWWNMMV#q&VYVVWYYYV"k"h"e"a"^"["Nw"Pt"Rq"Tn"Wk"K"I"G"E"C"* q"!+!#++*!" q  "q  "~q}} "! "zq"zzzzq1V9d5d9V5W1V5d"4V"m"n"n"o"oq-P5^1^5P1Q-P1^"0P"M"X"Xq&MXMMNXXXM"Kq"7M77LMM7"9"+ q*6,*66,"6q*7*,76*"y"m "V"k"Vq"VYVWYYYV"k"h"e"a"^"["N"P"R"T"W|"zq"zzzz"Eq"ENEFNMLE"q,,,""d"x"yq&xzxx"q"""{x qzx|xzx|x"eqzdxzx|xedzx"n"oq"oooo"q""kvqku|wkukw|w|uku"kz"q""a"^"["X"U"n q"dohdnooh"q"xxxz"i"l"n"q"t"v"|"h"mq"b"q"q""q&""" end %%EndProcSet 40 60 28 20 60 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 481 553 13 4 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C np 2464 1536 M 2436 1552 l 2436 1082 l 2464 1098 l cp f np 2843 1755 M 2843 1771 l 2840 1785 l 2436 1552 l 2464 1536 l cp f np 3223 1536 M 3237 1544 l 3237 1560 l 2900 1754 l 2843 1771 l 2843 1755 l cp f np 3223 1098 M 3251 1082 l 3251 1535 l 3237 1544 l 3223 1536 l cp f np 2843 878 M 2843 862 l 2868 860 l 3251 1082 l 3223 1098 l cp f np 2818 860 M 2843 862 l 2843 878 l 2464 1098 l 2436 1082 l cp f np 3268 2415 M 3270 2431 l 3256 2439 l 2860 2236 l 2872 2212 l cp f np 3637 2177 M 3665 2193 l 3285 2438 l 3270 2431 l 3268 2415 l cp f np 3616 1747 M 3629 1732 l 3643 1723 l 3665 2193 l 3637 2177 l cp f np 3643 1723 M 3629 1732 l 3572 1721 l 3237 1560 l 3237 1544 l 3251 1535 l cp f np 3572 1721 M 3629 1732 l 3616 1747 l 2840 1785 l 2843 1771 l 2900 1754 l cp f[1 3 2845 1827 2864 2168 ]Bd [1 4 2400 1573 2147 1719 ]Bd [1 4 3292 1515 3513 1396 ]Bd np 3082 669 M 3098 691 l 2868 860 l 2843 862 l 2843 845 l cp f np 3054 176 M 3074 148 l 3170 435 l 3144 443 l cp f np 2621 176 M 2601 148 l 3074 148 l 3054 176 l cp f np 2533 454 M 2507 446 l 2601 148 l 2621 176 l cp f np 2562 673 M 2578 651 l 2843 845 l 2843 862 l 2818 860 l cp f np 3331 2737 M 3241 2741 l 3256 2439 l 3270 2431 l 3285 2438 l cp f 1990 1050 310 1050 2 Ar [1 4 3709 2206 3941 2291 ]Bd 6990 970 4490 970 2 Ar np 7924 1536 M 7896 1552 l 7896 1082 l 7924 1098 l cp f np 8303 1755 M 8303 1771 l 8300 1785 l 7896 1552 l 7924 1536 l cp f np 8683 1536 M 8697 1544 l 8704 1556 l 8360 1754 l 8303 1771 l 8303 1755 l cp f np 8683 1098 M 8711 1082 l 8711 1521 l 8697 1544 l 8683 1536 l cp f np 8601 1138 M 8629 1138 l 8629 1497 l 8601 1497 l cp f np 8303 878 M 8303 846 l 8711 1082 l 8683 1098 l cp f np 8303 846 M 8303 878 l 7924 1098 l 7896 1082 l cp f np 8728 2415 M 8730 2431 l 8716 2439 l 8320 2236 l 8332 2212 l cp f np 9097 2177 M 9125 2193 l 8745 2438 l 8730 2431 l 8728 2415 l cp f np 9076 1747 M 9102 1717 l 9125 2193 l 9097 2177 l cp f np 8997 1819 M 9025 1817 l 9041 2141 l 9013 2143 l cp f np 9102 1717 M 9076 1747 l 8300 1785 l 8303 1771 l 8360 1754 l cp f[1 3 8305 1827 8324 2168 ]Bd [1 4 7860 1573 7607 1719 ]Bd np 8791 2737 M 8701 2741 l 8716 2439 l 8730 2431 l 8745 2438 l cp f np 8966 1384 M 8980 1408 l 8704 1556 l 8697 1544 l 8711 1521 l cp f np 8248 530 M 8276 530 l 8276 885 l 8248 885 l cp f np 8330 530 M 8358 530 l 8358 885 l 8330 885 l cp f np 7144 3136 M 7116 3152 l 7116 2682 l 7144 2698 l cp f np 7523 3355 M 7523 3371 l 7516 3383 l 7116 3152 l 7144 3136 l cp f np 7903 3136 M 7917 3144 l 7917 3160 l 7552 3370 l 7523 3371 l 7523 3355 l cp f np 7903 2698 M 7931 2682 l 7931 3136 l 7917 3144 l 7903 3136 l cp f np 7821 2738 M 7849 2738 l 7849 3097 l 7821 3097 l cp f np 7523 2478 M 7523 2446 l 7931 2682 l 7903 2698 l cp f np 7523 2446 M 7523 2478 l 7144 2698 l 7116 2682 l cp f np 7344 4067 M 7335 4082 l 7319 4079 l 7158 3663 l 7184 3653 l cp f np 7777 4044 M 7801 4070 l 7344 4096 l 7335 4082 l 7344 4067 l cp f np 7880 3654 M 7930 3580 l 7801 4070 l 7777 4044 l cp f np 7796 3650 M 7824 3658 l 7739 3982 l 7711 3974 l cp f np 7468 2130 M 7496 2130 l 7496 2485 l 7468 2485 l cp f np 7550 2130 M 7578 2130 l 7578 2485 l 7550 2485 l cp f np 8191 3286 M 8177 3310 l 7917 3160 l 7917 3144 l 7931 3136 l cp f[1 4 7080 3173 6827 3319 ]Bd np 7200 4373 M 7124 4325 l 7319 4079 l 7335 4082 l 7344 4096 l cp f np 7930 3580 M 7880 3654 l 7515 3383 l 7523 3371 l 7552 3370 l cp f[1 3 7479 3406 7215 3623 ]Bd np 7742 2497 M 7720 2479 l 7999 2121 l 8021 2139 l cp f np 7678 2447 M 7656 2429 l 7935 2071 l 7957 2089 l cp f np 7806 2547 M 7784 2529 l 8063 2171 l 8085 2189 l cp f 4170 4030 6390 3810 2 Ar np 2994 4406 M 2966 4422 l 2966 3952 l 2994 3968 l cp f np 3373 4625 M 3373 4641 l 3366 4653 l 2966 4422 l 2994 4406 l cp f np 3753 4406 M 3767 4414 l 3767 4430 l 3402 4640 l 3373 4641 l 3373 4625 l cp f np 3753 3968 M 3781 3952 l 3781 4406 l 3767 4414 l 3753 4406 l cp f np 3671 4008 M 3699 4008 l 3699 4367 l 3671 4367 l cp f np 3373 3748 M 3373 3716 l 3781 3952 l "q" q"     " q"        "q   "q" q"""""""" q"    "q""""""""""""q"""$q"%%%%%"&q&%9899'%%8"v9q"v8:v8v::98v8"x4"j% qj%v:k%j%v:v8k%"v""2"8q2:7:327"3": q"9GGF99:G"" """" q&  "7q"%::7%%':"""""!"#"g$"d#"`#"]""Y"" q"" q" "q"݅o3753 3968 l cp f np 3373 3716 M 3373 3748 l 2994 3968 l 2966 3952 l cp f np 3194 5337 M 3185 5352 l 3169 5349 l 3008 4933 l 3034 4923 l cp f np 3627 5314 M 3651 5340 l 3194 5366 l 3185 5352 l 3194 5337 l cp f np 3730 4924 M 3780 4850 l 3651 5340 l 3627 5314 l cp f np 3646 4920 M 3674 4928 l 3589 5252 l 3561 5244 l cp f np 4038 4554 M 4024 4578 l 3767 4430 l 3767 4414 l 3781 4406 l cp f[1 4 2928 4444 2665 4595 ]Bd np 3058 5631 M 2982 5583 l 3169 5349 l 3185 5352 l 3194 5366 l cp f np 3780 4850 M 3730 4924 l 3365 4653 l 3373 4641 l 3402 4640 l cp f[1 3 3329 4676 3065 4893 ]Bd [1 4 3373 3677 3373 3400 ]Bd 3130 8190 350 8190 2 Ar np 5484 7926 M 5456 7942 l 5456 7472 l 5484 7488 l cp f np 5863 8145 M 5863 8161 l 5856 8173 l 5456 7942 l 5484 7926 l cp f np 6243 7926 M 6257 7934 l 6257 7950 l 5892 8160 l 5863 8161 l 5863 8145 l cp f np 6243 7488 M 6271 7472 l 6271 7926 l 6257 7934 l 6243 7926 l cp f np 6161 7528 M 6189 7528 l 6189 7887 l 6161 7887 l cp f np 5863 7268 M 5863 7236 l 6271 7472 l 6243 7488 l cp f np 5863 7236 M 5863 7268 l 5484 7488 l 5456 7472 l cp f np 5684 8857 M 5675 8872 l 5659 8869 l 5498 8453 l 5524 8443 l cp f np 6117 8834 M 6141 8860 l 5684 8886 l 5675 8872 l 5684 8857 l cp f np 6220 8444 M 6270 8370 l 6141 8860 l 6117 8834 l cp f np 6136 8440 M 6164 8448 l 6079 8772 l 6051 8764 l cp f np 6535 8078 M 6521 8102 l 6257 7950 l 6257 7934 l 6271 7926 l cp f[1 4 5419 7963 5162 8111 ]Bd np 5460 9288 M 5428 9254 l 5384 9238 l 5659 8869 l 5675 8872 l 5684 8886 l cp f np 6270 8370 M 6220 8444 l 5855 8173 l 5863 8161 l 5892 8160 l cp f[1 3 5819 8196 5555 8413 ]Bd [1 4 5863 7197 5863 6920 ]Bd np 5573 9507 M 5549 9519 l 5429 9285 l 5428 9254 l 5460 9288 l cp f np 5040 9248 M 5042 9220 l 5384 9238 l 5428 9254 l 5406 9267 l cp f np 5303 9535 M 5277 9523 l 5406 9267 l 5428 9254 l 5429 9285 l cp f 9810 8150 7103 8150 2 Ar gr count origstk sub{P}rp end chemsave restore ,  Helvetica .+S]H *+ 3 +(]aC(GCH +3 ("O("wO+)sCOOMe(zOH(]dH *+ 3 +(]rC(GCH +3 (COOH(O(isO+(DCH +3 (=H *+ 3 +(KC(BHOOC(CH +3 (mH *+ 3 +({C(#kMeOOC(OH(+ NaBH + 4 (HCH +3 (H *+ 3 +(C(1. CH +"2 `(N -+ 2 (2. LiAlH(t-BuO) /+U3 (X OAc(%HCl(CH +3 (H *+ 3 +(C+HO(Z*15. Sodium borohydride as reducing agent * #16. Mechanism of reaction process * &17. Alkoxyhydrides as reducing agents+1. CH ׀+%3 ([MgI(02. Ac .+2 /`(TO(}Li/ EtNH -+-2 (-18. Acetylation, influence of substitution * 19. Metal amine reductionsd CHMDSTRG ,  x(<<@* X/Tv  Dh &\8   % 8 T % < u M7'?F   =F  + ; '812 y3"48"5T y6 = u"$>#?#@gF'#H yO xR >S !mT >U ;";K xV mW@ ^_w`ame ! h [jflHTp =qn w4 x 7y4zn{ 7|6  {A  7K %\ .hh{.{J "5" o$>% $x%s            !",(789:;<GABCPEDN X !Y!"Z"$[$%\%]#L./r&'b'(c()d!&o%*f"+i ,k'-m!)n01}12~23344505677889265:3;1<7=29>??@@AABBC>CDEEFFG@DCHAI?JEK@GKLKMKN CH3 CH3 OOOHCOOMeCH3CH3O#COOH*O+CH3[,CH3-COOH:OH;CH3<CH3=COOMeHOAcICH3JCH3LCH3MCH3NOH ` :\%4 `  & x `  .$ D  `  Q# g  `  t- t `  )  ` :. ` #/0#<$ `  I< +  `  !J ! $ ` ( Q|0 `  { g 0 ! `n  zs  | ` MP  `   t l $ ` qu ` p n P `  p  ` ,L `  1| lD `  0(|\ l ` & %X&HH ` $_#$ ` & %Xt&   . HPNaBH4  (|HCl *n  `H  V H \D 1. CH2N2  2. LiAlH(t-BuO)3s  @8*Ms15. Sodium borohydride as reducing agent 16. Mechanism of reaction process 17. Alkoxyhydrides as reducing agents   n ` ,xh 1. CH3MgI   n `b !  X!H02. Ac2O   . (! Li/ EtNH2I  *D)+H-I18. Acetylation, influence of substitution 19. Metal amine reductions Helvetica3 ix xl 3 -1 r s 3 1 r e s o o at ro D m e D m a sq}b/OB{/bS x OP D bS dv D lW 2 m lt{P lW 2 m}if/bd x}b/DA{np 0 0 M aL 0 aR aL m 180 aA s 180 aA a arc cp f}b/OA{np 0 cw -2 dv M aL 0 aR aL m 180 aA s 180 arc 0 cw -2 dv rlineto cp f}b/Ast{SM cw 0.8 m sl st}b/SA{aF m lW m/aL x 0.263/aR x aL 1 aR s m np 0 p M rad 0 p l gs Ast gr}b/CA{aF lW m 0.8 m/aL x 0.316/aR x aL 1 aR s m 2 dv rad D m o D m s D 0 le{P P P}{sq at 2 m np rad 0 rad 180 6 -1 r s 180 6 -1 r s arc gs Ast gr cpt e at ro}ie}b/AA{np rad 0 rad 18 @ @J$ @ @   !" P $&p&r'9:]:^:_:` HH(FG(HH(d'`=/R@H-:LaserWriter 8 New YorkEE5 hinesol.mswdCollege Use OnlyCollege Use Only