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Simultaneous inversion of configurations of C 22 , C 23 in 24 S ‐ethyl‐3,5‐cyclo‐cholestane‐22 S ,23 S ‐diol‐6‐one
Author(s) -
Liu XingPing,
Li YuLin,
Liang XiaoTian
Publication year - 1989
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19890070312
Subject(s) - chemistry , cholestane , regioselectivity , diol , yield (engineering) , hydrolysis , inversion (geology) , epoxide , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , thermodynamics , paleontology , structural basin , biology , physics
In this paper, obtainment of 3 by simultaneous inversion of configurations of C 22 , C 23 , in 2 via its ditosylate or dimesylate was unsuccessful, leading to elimination products instead. However, monotosylate of 2 can be readily obtained with exclusive regioselectivity, which in turn gave a single epoxide 7b Hydrolysis of 7b gave 3 and 2 is a ratio of 2:1, with a combined yield of 80%. The‐recovered 2 can of course be recycled again.