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

1 January 1976

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1

No. 17,p. 1889-1893
https://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.

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