Syntheses of derivatives of oestrane and 19-norsteroids from 6-Methoxytetralone (cas 1078-19-9) and 6-hydroxytetralone

Add time:08/11/2019    Source:sciencedirect.com

The corresponding derivatives of Δ1,3,5(10),9,(11)-8,14-seco-d-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 Δ1,3,5(10),8,14-d-homo-oestrapentaen-3-ol-17a-one (XIII), and the diketone (VII) may be converted, according to conditions, into 3-methoxy-Δ1,3,5(10),8,14-d-homo-oestrapentaen-17a-one (X), 3-methoxy-Δ1,3,5(10),9,(11)-d-homo-oestratetraen-14-ol-17a-one (XIV), and d-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 d-homo-oestrone and 8-iso-d-homo-oestrone XIX and XVII which have been converted into the methyl ethers of (±)-oestrone and 8-iso-oestrone (XX and XXI). 19-Nor-d-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.

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