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Labeled bile acids IV: Base‐catalyzed one‐pot synthesis of deuterium labeled bile acids
Author(s) -
Lai Chee Kong,
Byon Chang Yon,
Gut Marcel,
Nagahisa Atsushi
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210704
Subject(s) - chemistry , deuterium , catalysis , steric effects , ketone , base (topology) , alcohol , keto–enol tautomerism , sodium , organic chemistry , butanol , medicinal chemistry , ethanol , mathematical analysis , physics , mathematics , quantum mechanics
Deuterium labeled bile acids are synthesized from their keto acid analogs by a one‐pot base‐catalyzed enolization exchange with deuterated hydroxylic solvents (OD) followed by in situ reduction of the ketone. The stereochemistry of the alcohol, especially that at C‐7, can be controlled either by steric approach reduction with sodium borodeuteride or thermodynamically by reduction with sodium in n ‐butanol.