Camphoric acid derived organocatalysts: Efforts toward the asymmetric synthesis of the unnatural enantiomer of the taxol C-13 side-chain and the calcium antagonist diltiazem

CHED 531

Kelly A. Mesch and Shawn R. Hitchcock, hitchcock@ilstu.edu. Department of Chemistry, Illinois State University, 214 Julian Hall, Campus Box 4160, Normal, IL 61790-4160
Organocatalysts are reagents that are gaining much popularity due to the success of these compounds in catalytic asymmetric aldol reactions, conjugate addition reactions, and other transformations. Our research group has become interested in pursuing novel organocatalyst agents that might prove to be more effective than current literature models. The asymmetric template of interest is based on commercially available camphoric acid. Camphoric acid is converted to the corresponding anhydride by reaction with toluenesulfonyl chloride and potassium carbonate. Reaction of the anhydride with (1R-2S)-norephedrine yields a gamma-amido acid that has a rigid structure that can be exploited for the purpose of conducting asymmetric syntheses. This poster presentation will present our work on developing organocatalysts from camphoric anhydride.