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Communication | Special issue | Vol 66, No. 1, 2005, pp.61-68
Published online, 22nd September, 2005
DOI: 10.3987/COM-05-S(K)17
A New Asymmetric Total Synthesis of Enantiopure (-)-Malyngolide

Hidetoshi Miyamoto, Mitsuhiro Iwamoto, and Masahisa Nakada*

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

A new asymmetric total synthesis of (-)-malyngolide is described. This synthesis is based on the originally developed catalytic asymmetric IMCP reaction; that is, α-diazo-β-keto sulfone (13) was successfully converted to cyclopropane (12) in 92 % yield with excellent enantioselectivity (97% ee), and cyclopropane (12) was successfully converted to (-)-malyngolide.