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

Bijoy, Panicker ; Ramachandran, Uma ; Subba Rao, G. S. R. (1994) Direct conversion of 13β-alkylgonatetraenes into 13β-alkylgon-4-en-3-ones Journal of the Chemical Society, Perkin Transactions 1 (16). pp. 2331-2333. ISSN 1472-7781

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Official URL: http://pubs.rsc.org/en/content/articlelanding/1994...

Related URL: http://dx.doi.org/10.1039/P19940002331

Abstract

Birch reduction of 8, 9-didehydroestradiol-17β 3-methyl ether 1 or 9(11)-didehydroestradiol-17β 3-methyl ether 2 followed by acid hydrolysis results in a mixture of 19-nortestosterone 8 and 19-nor-9β, 10α-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, 18α-homo-19-nortestosterone 12 is prepared from the acetate of 18a-homoestradiol-17β 3-methyl ether, 10.

Item Type:Article
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