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Direct conversion of 13-beta-alkylgonatetraenes into 13-beta-alkylgon-4-en-3-ones

Bijoy, P and Ramachandran, U and Rao, GSRS (1994) Direct conversion of 13-beta-alkylgonatetraenes into 13-beta-alkylgon-4-en-3-ones. In: Perkin transactions 1 (16). 2331-2333 .

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Birch reduction of 8,9-didehydroestradiol-17 beta 3-methyl ether 1 or 9(11)-didehydroestradiol-17 beta 3-methyl ether 2 followed by acid hydrolysis results in a mixture of 19-nortestosterone 8 and 19-nor-9 beta, 10 alpha-testosterone 9 in varying amounts. However, reduction of their acetates with sodium or lithium, tert-butyl alcohol in liquid ammonia and in the presence of aniline affords exclusively 19-nortestosterone. Similarly, 18a-homo-19-nortestosterone 12 is prepared from the acetate of 18a-homoestradiol-17 beta 3-methyl ether, 10.

Item Type: Journal Article
Publication: Perkin transactions 1
Publisher: Royal Society of Chemistry
Additional Information: Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 02 Jun 2011 04:51
Last Modified: 02 Jun 2011 04:51
URI: http://eprints.iisc.ac.in/id/eprint/36412

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