Model studies for the synthesis of taxoid side-chains.

Abstract

The objectives of this thesis were to make progress toward the synthesis of the side-chain of paclitaxel. The model systems chosen were benzoyl-1,3-dithiane, (1-phenyl-2-(1,3-dithiacyclohexyl)ethanone) and hydrocinnamoyl-1,3-dithiane, (4-phenyl-1-(1,3-dithiacyclohexyl)butan-2-one). This work consisted of screening several acyl equivalents to determine which one could best be used for a one carbon homologation. Enantioselective reduction of the carbonyl group, using three different chiral reducing agents, was also studied. Studies were also conducted to determine the most efficient manner in which to unmask the carbonyl group and convert it to the more stable methyl ester. (Abstract shortened by UMI.)