Synthesis of des-A-B-secocholestanes

Two independent synthetic routes to 10-oxo-5, 10-seco-des-A-cholestan-5-oic acid ( 5 ) are described. The route including the Baeyer-Villiger rearrangement of (10R)-des-A-cholestan-5-one ( 2 a), followed by hydrolysis of the lactone 3 a obtained and oxidation of the C-10 hydroxyl group, seems to be...

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Veröffentlicht in:Canadian journal of chemistry 1984-06, Vol.62 (6), p.1081-1084
Hauptverfasser: Szczepek, Wojciech J, Morzycki, Jacek W, Bończa-Tomaszewski, Zbigniew, Chodyński, Michał, Rodewald, Władysław J
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Sprache:eng
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Zusammenfassung:Two independent synthetic routes to 10-oxo-5, 10-seco-des-A-cholestan-5-oic acid ( 5 ) are described. The route including the Baeyer-Villiger rearrangement of (10R)-des-A-cholestan-5-one ( 2 a), followed by hydrolysis of the lactone 3 a obtained and oxidation of the C-10 hydroxyl group, seems to be superior to ozonolysis of the 5(10)-enol acetate 6 of des-A-ketone which resulted in the formation of 5,10-seco-des-A-19-norcholestan-5,10-dioic acid ( 7 ), in addition to the compound 5 . Product 7 and its 6-nor analog 12 have also been obtained by ruthenium tetroxide oxidation of the respective A-ring phenols 8 , 9 , and 11 .
ISSN:0008-4042
1480-3291
DOI:10.1139/v84-178