Asymmetric Synthesis of SM-9164, a Biologically Active Enantiomer of Antifungal Agent SM-8668
6 Citations•1996•
H. Miyauchi, Toshio Nakamura, N. Ohashi
Bulletin of the Chemical Society of Japan
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Abstract
SM-9164, a biologically active enantiomer of antifungal agent SM-8668, was prepared by asymmetric synthesis in 10 steps in 13% overall yield from commercially available 2-chloro-1-(2,4-difluorophenyl)ethanone. The crucial steps were Katsuki-Sharpless asymmetric epoxidation of the (E)-allylic alcohol and epimerization of the erythro-sulfone to the desired threo-isomer under basic conditions.