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■ A New Synthetic Approach to a Fungal β-Lactone Based on the Asymmetric [2,3]-Wittig Rearrangement

Katsuhiko Tomooka, Takahiro Takeda, Au Wing Kuen, and Takeshi Nakai*

*Department of Chemical Technology, Faculty of Engineering, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan

Abstract

An asymmetric synthesis of the chiral β-lactone precursor of the HMG-CoA synthase, inhibitor L-659,699, is described, which involves as the key step an asymmetric [2,3]-Wittig rearrangement to control the stereogenic centers at the ring carbons (C2’ and C3’).