Anti-selective aldol reactions of N-glycolyloxazolidinethiones with acetaldehyde: Synthesis of the de-oxygenated sugars of apoptolidin

ORGN 103

Michael T. Crimmins, Department of Chemistry, University of North Carolina at Chapel Hill, Venable and Kenan Laboratories of Chemistry, CB# 3290, Chapel Hill, NC 27599 and Alan Long, Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290.
Addition of excess titanium tetrachloride to the aldol reaction mixtures of N-glycolyloxazolidinethiones with aldehydes provides the non-Evans anti isomers in good yields and diastereoselectivities. Subsequent protection and manipulation of three acetaldehyde-adducts gives key carbonyl compounds that are then elaborated to afford the de-oxygenated carbohydrate units of the apoptosis inducing natural product apoptolidin.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004