Bulletin of the Chemical Society of Japan p. 2625 - 2632 (1996)
Update date:2022-07-30
Topics:
Miyauchi, Hiroshi
Nakamura, Toshio
Ohashi, Naohito
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.
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Doi:10.1139/v68-181
(1968)Doi:10.1246/bcsj.40.2641
(1967)Doi:10.1007/BF01431612
(1996)Doi:10.1021/jo00118a021
(1995)Doi:10.1055/s-2002-33531
(2002)Doi:10.1016/0040-4039(96)01788-1
(1996)