Syntheses of derivatives of oestrane and 19-norsteroids from 6-methoxytetralone and 6-hydroxytetralone

The corresponding derivatives of Δ^{1,3,5(10),9,(11)}-8,14-seco- -homo-oestratetraen-3-ol-14,17a-dione(VII, VIII, IX) have been obtained by the condensation of 3-methoxy-, 3-hydroxy-, and 3-tetrahydropyranyloxy-1-vinyltetralols (IV, V, VI) with methyldihydroresorcinol. The diketones VIII and IX cyclize to form Δ^{1,3,5(10),8,14}- -homo-oestrapentaen-3-ol-17a-one (XIII), and the diketone (VII) may be converted, according to conditions, into 3-methoxy-Δ^{1,3,5(10),8,14}- -homo-oestrapentaen-17a-one (X), 3-methoxy-Δ_{1,3,5(10),9,(11)}- -homo-oestratetraen-14-ol-17a-one (XIV), and -homoequilenin (XI). Hydrogenation of the ketones X and XIII leads to the dihydroketones XV and XVI with a trans junction of the C and D rings. Reduction or hydrogen of XV gives the methyl ethers of -homo-oestrone and 8-iso- -homo-oestrone XIX and XVII which have been converted into the methyl ethers of (±)-oestrone and 8-iso-oestrone (XX and XXI). 19-Nor- -homotestosterone (XXV) and its methyl and ethyl analogues, which possess anabolic activity, have been obtained by a series of reactions from the ketones X and XV.