Nasipuri, Dhanonjoy ; Ghosh, Sanat K. (1976) Heterocyclic steroids. Part II. Synthesis of (±)-8-hydroxy-3-methoxy-11-aza-18-norestra-1,3,5(10),9(11)-tetraen-17-one and related compounds Journal of the Chemical Society, Perkin Transactions 1 (17). pp. 1889-1893. ISSN 0300-922X
Full text not available from this repository.
Official URL: http://www.rsc.org/publishing/journals/article.asp...
Related URL: http://dx.doi.org/10.1039/P19760001889
Abstract
5-Oxo-2-(1,2,3,4-tetrahydro-6-methoxy-2-naphthyl)cyclopent-1-enylacetic acid (II), readily available from 2-acetyl-1,2,3,4-tetrahydro-6-methoxynaphthalene (I), was hydrogenated and then oxidised with chromic acid to give the dioxo-acid (IV). By a modified Curtius rearrangement this afforded (±)-9(11)-didehydro-8-hydroxy-11-aza-18-norestrone 3-methyl ether (IX), the hydroxy-group being presumably introduced through autoxidation. In contrast, similar treatment of the 13-methyl acids (V) and (VI) of the natural series gave the 3-methyl ethers of 9(11)-didehydro-11-aza-estrone (X) and -17β-estradiol (XI), which do not undergo oxidation in air.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 27181 |
| Deposited On: | 10 Dec 2010 12:59 |
| Last Modified: | 04 Mar 2011 04:47 |
Repository Staff Only: item control page
