Steroid hormones. Part XIX. (+)-9β-Androstenedione and ‘retro’-androstenedione from 9β-oestrone
Abstract
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.