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A Formal Synthesis of Betamethasone
Author(s) -
Wang Shasha,
Shi Yong,
Tian Weisheng
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500335
Subject(s) - chemistry , triol , hydroxylation , bromide , halogenation , betamethasone , pregnane , allyl bromide , side chain , organic chemistry , stereochemistry , diol , enzyme , polymer , immunology , biology
A formal synthesis of betamethasone from 5 α ‐pregnane‐3 β ,16 β ,20 S ‐triol is described. Key transformations are a bromination‐acetylation of triol, an S N 2 reaction of the resulting C16 α ‐bromide with dimethylcopperlithium to get the required C16 β ‐methyl group, and a double hydroxylation to prepare the dihydroxyacetone side chain.