Steroid hormones. Part XIX. (+)−9β-Androstenedione and 'retro'-androstenedione from 9β-oestrone

Birch, A. J. ; Subba Rao, G. S. R. (1967) Steroid hormones. Part XIX. (+)−9β-Androstenedione and 'retro'-androstenedione from 9β-oestrone Journal of the Chemical Society C: Organic . pp. 2509-2510. ISSN 0022-4952

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Addition of dibromocarbene to the 5(10)-double bond of the bisketal produced by the action of ethylene glycol and acid on 1,4-dihydro-9β-oestrone 3-methyl ether 17-(ethylene ketal), followed by reduction and fission of the cyclopropane ring leads chiefly to (+)-9β-androst-4-ene-3,17-dione, but the product contains some 'retro'-androstenedione.

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