- Meeting Time: Tuesday : 11:45 - 12:25; Thursday: 12:15 - 1:50
- Office hours: Open and by arrangement
- Text: None.
Handouts will be provided for each class. These will include color printouts of synthesis schemes; writeups of important general topics, and a summary of named reactions and reagents.
Chem 432 is an introduction to the art and methodology of organic synthesis. This is the proving ground for all you know about organic chemistry. The many reactions must now be placed in a proper sequence. The impact of stereochemistry can be felt on almost every reaction. The relative reactivities of multiple functional groups will require rethinking of the sequencing of steps. Instrumental and chemical methods for determining product composition will be needed for every transformation. And for the modern synthesis chemist we will need to know molecular modeling: how to determine a preferred conformation; where is the calculated site of reaction; is the reaction allowed within the framework of Frontier Molecular Orbital Theory. There is much to synthesize besides the molecule of interest!
For this course we will use a number of natural products as targets for showing how others have designed syntheses. We will exam each step, reviewing reagents, analyse stereochemical consequences, and revisiting mechanisms for many processes. As we rapidly develop our tools (reactions and reagents) of synthesis, we will then start examining the use of retrosynthetic analysis to guide us in our synthesis plan.
We will have a quiz at the start of each lecture session. The quiz will consist of three questions selected by drawing in the class: (1) a question on a named reaction from the accumulated reactions to date, (2) a question from the accumulated reagent list, and (3) a mechanism for one of the reaction types. The major portion of the grade will be for your efforts in developing a total synthesis of a recently discovered (but not yet syntheisized) natural product. After developing your reaction scheme you will be expected to write it up in the format of a Tetrahedron Letters publication, where you have assumed all of your reactions work! References for important background will be required. This "publication" will be reviewd by three "outside" reviewers and a recommendation about publication will be made. This paper will constitute the final exam for the course. Quiz grades will count as 40% of your grade, the final will count as 60% of your grade.