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Secosteroids. I. Synthesis of vic-Diols in B-Secocholestane Group (1988)

Rodewald, W. J. ; Piotrowski, G. T.

New York, NY : Wiley-Blackwell

Journal für Praktische Chemie/Chemiker-Zeitung 330 (1988), S. 775-781

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ISSN: 0021-8383

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The transformation of 3-β-methoxycholest-5-en-7-on 1 into B-secodiols 10, 11 and 12 is described. Reduction of lactone 2, obtained from 1, yielded diol 5 which was acetylated to monoacetate 6. The latter, after dehydration to a mixture of olefins and its hydroxylation, afforded the final products 10, 11 and 12. It has been established that in the reaction of monoacetate 6 with phosphorous oxychloride in pyridine in addition to the β-elimination, migration of a double bond and Wagner-Meerwein rearrangement occur.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/prac.19883300513

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