Facile Synthesis of 5α-Fluorocholestan-3-one from 4-Cholesten-3-one via Molecular Fluorine Addition and Reductive Defluorination

Akemi TOYOTA; Jun CHIBA; Yoshiaki SUGITA; Masayuki SATO; Chikara KANEKO

doi:10.1248/cpb.42.459

Akemi TOYOTA, Jun CHIBA, Yoshiaki SUGITA, Masayuki SATO, Chikara KANEKO

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Keywords: fluorination, molecular fluorine, 5α-fluorocholestan-3-one, reductive defluorination, triphenyltin hydride

JOURNAL FREE ACCESS

1994 Volume 42 Issue 3 Pages 459-461

DOI https://doi.org/10.1248/cpb.42.459

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Abstract

A facile synthesis of 5α-fluorocholestan-3-one from 4-cholesten-3-one has been accomplished. Direct fluorination of the enone by molecular fluorine gave the cis-vicinal difluoride. Treatment of this adduct with triphenyltin hydride in the presence of azobisisobutyronitrile afforded the title compound.

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