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Acid‐Catalysed Backbone Rearrangement of cholesta‐6,8(14)‐dienes
Author(s) -
Liu RongMing,
Chillier Xavier F. D.,
Kamalaprija Philippe,
Burger Ulrich,
Gülaçar Fazil O.
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790407
Subject(s) - chemistry , epimer , anhydrous , sulfonic acid , acetic acid , toluene , computational chemistry , stereochemistry , organic chemistry , medicinal chemistry
Rearrangement of 5α‐ and 5β‐cholesta‐6,8(14)‐dienes ( 13a and 13b , resp.) in the presence of anhydrous toluene‐4‐sulfonic acid in acetic acid leads to 5α‐ and 5β‐12(13 → 14)‐ abeo ‐cholesta‐8,13(17)‐dienes ( 15a and 15b , resp.) via 5α‐ and 5β‐cholesta‐8,14‐dienes ( 14a and 14b , resp.), respectively. Epimerization at C(20) of the spirosteradienes 15a and 15b occurs with increasing reaction time. Molecular‐mechanics calculation of the relative stabilities of these compounds and of congeners thereof is in agreement with the observed reaction pathway.