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Regio‐ and Stereoselective “Long‐Range” Hydroxylation of Cholestanes–A Novel Route to 5α‐Steroids with cis ‐Coupled A, B‐Rings
Author(s) -
Bégué JeanPierre
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198106101
Subject(s) - stereoselectivity , hydroxylation , yield (engineering) , cyclohexane , chemistry , bromide , stereochemistry , organic chemistry , catalysis , materials science , enzyme , metallurgy
Regio‐ and stereoselective synthesis via carbenium ions seldom succeed so well as the γ‐hydroxylation of cyclohexane derivatives via α‐acylcarbenium ions. This method can also be applied to cholestanes: the bromide (1) , affords the hydroxyketone (2) in 45% yield.
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