Tetrahedron

Diastereo-and enantioselective synthesis of 4-and 3, 4-substituted 2-acetoxy-butyrolactones

D Enders, H Sun, FR Leusink

Index: Enders, Dieter; Sun, Hongbin; Leusink, Frederik R. Tetrahedron, 1999 , vol. 55, # 19 p. 6129 - 6138

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Citation Number: 16

Abstract

An efficient asymmetric synthesis of 4-mono-and 3, 4-disubstituted 2-acetoxy-butyrolactones 2 has been developed, based on a hydrazone-mediated asymmetric aldol reaction, an intramolecular lactonization and a stereoselective hydrogenation of the resulting butenolides 1. An application of this process in the synthesis of the natural hunger substance 3 (ee= 90%) is also presented.

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