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Steroids and sex hormons. Part 264 . Lewis acid catalyzed reversible [1,5]‐hydride shift in 3,19‐epoxy‐steroids
Author(s) -
Acklin Georg,
Graf Walter
Publication year - 1980
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.19800630825
Subject(s) - chemistry , boron trifluoride , hydride , intramolecular force , lewis acids and bases , catalysis , stereoselectivity , epoxy , steroid , medicinal chemistry , boron , stereochemistry , organic chemistry , hormone , hydrogen , biochemistry
3β, 19‐Epoxy‐3 α‐methoxy‐steroids ( e.g. 1 , Scheme 1 ) are converted into the corresponding 3 α‐methoxy‐19‐oxo compounds ( e.g. 3 ) in the presence of boron trifluoride etherate, via an intramolecular hydride ion transfer from C (19) to (3) which is shown to be an equilibrium process. By subjecting the specifically deuteriated (19 S )‐ and (19 R )‐compounds 1b and 1c to this reaction it was shown to be highly stereoselective.