DIRECT CONVERSION OF 13-BETA-ALKYLGONATETRAENES INTO 13-BETA-ALKYLGON-4-EN-3-ONES

Authors
BIJOY P RAMACHANDRAN U RAO GSRS
Citation
P. Bijoy et al., DIRECT CONVERSION OF 13-BETA-ALKYLGONATETRAENES INTO 13-BETA-ALKYLGON-4-EN-3-ONES, Journal of the Chemical Society. Perkin transactions. I, (16), 1994, pp. 2331-2333
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
16
Year of publication
1994
Pages
2331 - 2333
Database
ISI
SICI code
0300-922X(1994):16<2331:DCO1I1>2.0.ZU;2-O
Abstract
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 hyd rolysis results in a mixture of 19-nortestosterone 8 and 19-nor-9 beta , 10 alpha-testosterone 9 in varying amounts. However, reduction of th eir acetates with sodium or lithium, tert-butyl alcohol in liquid ammo nia and in the presence of aniline affords exclusively 19-nortestoster one. Similarly, 18a-homo-19-nortestosterone 12 is prepared from the ac etate of 18a-homoestradiol-17 beta 3-methyl ether, 10.