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A Study of the Reactivity of Polyhydroxylated Sterol Derivatives
Author(s) -
Marek Aleš,
Klepetářová Blanka,
Elbert Tomáš
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500138
Subject(s) - chemistry , silylation , reactivity (psychology) , dimethyldioxirane , alcohol , organic chemistry , substrate (aquarium) , lithium (medication) , hydride , chloride , alcohol oxidation , medicinal chemistry , catalysis , metal , medicine , oceanography , alternative medicine , pathology , endocrinology , geology
A detailed study of regiospecific silylation, oxidation, and reduction of sterols is reported. The different reactivity of 2α and 3α hydroxy groups is demonstrated on a 2α,3α‐dihydroxy‐5α‐pregnane‐6,20‐dione as a model substrate. A regiospecific silylation of the 2α‐alcohol occurred when silyl chloride was used under mild reaction conditions. The selective oxidation of one of the 2α,3α‐diols by dimethyldioxirane or the Dess–Martin periodinane led to a mixture of α‐hydroxyketones with high prevalence of 3,6,20‐trione over 2,6,20‐trione in the ratio 10:1. A regiospecific reduction of a model substrate by lithium tri‐ tert ‐butoxyaluminium hydride gives the C6 alcohol.