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Communication | Special issue | Vol 25, No. 1, 1987, pp.105-108
Published online, 1st January, 1970
DOI: 10.3987/S-1987-01-0105
A Chiral, Non-racemic C1-C7 Erythronolide Synthon Using the 3-Methyl-γ-butyrolactone Strategy

Frederick E. Ziegler and Alyssa Kneisley

*Sterling Chemistry Laboratory, Yale University, 225 Prospect St., New Haven, CT 06511, U.S.A.

Abstract

A chiral, non-racemic C1-C7 unit for the synthesis of the erythronolides has been prepared. R-3-Methyl-γ-butyrolactone serves as the template for the synthesis. The stereochemistry at C3 of the synthon 13 was established by stereoselective , kinetic protonation of the enolates of lactones 9 and 10.