Date

2014

Department or Program

Chemistry

Primary Wellesley Thesis Advisor

David Haines

Abstract

Lactacystin, or more specifically, its biologically active form, omuralide, is a known inhibitor of cell cycle progression in a number of cell lines. However, omuralide is also an inhibitor of the proteasome, an essential protease within eukaryotic cells. Because of the complexity of the available syntheses, development of selective analogs of omuralide has progressed slowly. Our research seeks to develop efficient and highly stereoselective syntheses of omuralide analogs via the metal catalyzed reaction of a chiral aldehyde with a protected oxazole.This catalysis has been accomplished with high stereoselectivity using a simple aluminum catalyst but the efficiency of this reaction has not been high. Results from a variety of additional catalysts will be discussed.

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