Kole, P. ; Ray, S. ; Kamboj, V. P. ; Anand, N. (1975) Studies in antifertility agents. 11. secosteroids. 5. synthesis of 9,11-secoestradiol Journal of Medicinal Chemistry, 18 (7). pp. 765-766. ISSN 0022-2623
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jm00241a026
Related URL: http://dx.doi.org/10.1021/jm00241a026
Abstract
9,11-Secoestradiol (9) and 11-hydroxy-9,11-secoestradiol (12) have been synthesized starting from 17-acetoxyestradiol 3-methyl ether (1) and found to possess significant antifertility activity in rats. 3-Methoxy-9,11-seco-9-oxo-17beta-acetoxyestra-1,3,5(10)-trien-11-oic acid (2), prepared by CrO3 oxidation of 1, on hydrogenolysis gave methyl 17beta-hydroxy-3-methoxy-9,11-secoestra-1,3,5(10)-triene-11-carboxylate (3). The 17-O-THP derivative of 3 was treated with LiAlH4 to give 17beta-(O-tetrahydropyranyl)-3-methoxy-11-hydroxy-9,11-secoestra-1,3,5(10)-triene (5). The 11-O-mesylate of 5 on LiAlH4 reduction followed by mild acid treatment and demethylation under alkaline conditions gave 9. LiAlH4 reduction of 3 gave 9,11-seco-11-hydroxyestradiol 3-methyl ether (11) which on demethylation gave 9,11-seco-11-hydroxyestradiol (12).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 96956 |
| Deposited On: | 11 Feb 2013 07:22 |
| Last Modified: | 11 Feb 2013 07:22 |
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