CHED 263

Catechol approach to natural products

Michelle E. Weber, Sean T. Neville, and Bradford P. Mundy. Chemistry Department, Colby College, Mayflower Hill, Waterville, ME 04901, fax: 207-872-3804,

The current focus of our group is the synthesis of natural products through an electrophilic aromatic substitution approach using substituted catechols as building blocks. The first of the two target molecules being studied is a dimer of herbertene diol, commonly known as MastigophoreneŻA, that is found in a number of liverworts. This molecule has been shown to have pronounced activity in helping to develop new neuron connections. 1Ż(2,3Żdihydroxyphenyl)Ż4ŻmethoxyŻ1Żbutanone, an iron chelator, is the other molecule being investigated. Based on preliminary mass spectral and nmr data, the working structure for this constituent of Brown Rot fungus (Gloephyllum trabeum) is shown below. Our current electrophilic aromatic substitution protocols will be contrasted other methods that are more traditional, and that have been successfully used by our group in the past. We will also focus on the development of model compounds for these reactions and include a discussion of the mechanistic and regiochemical analysis of our work.