Process for the preparation of gestodene

C - Chemistry – Metallurgy – 07 – J

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C07J 1/00 (2006.01) C07J 21/00 (2006.01)

Patent

CA 2157076

Process for preparing Gestodene from (-)estra-1,3,5(10),8-tetraen-3- methoxy-18-methyl-17.beta.-hydroxy, comprising the following steps: a) hydrogenation of the double bond in 8(Li in liquid NH3 in presence of aniline); b) hydrogenation of a double bond of the aromatic ring (Li in liquid NH3 in presence of ter.butanol); c) hydrolysis of the methoxyl in 3 with introduction of a ketonic group and transposition of the double bond from 5-10 to 4-5; d) conversion of the ketonic group in 3 to acetalic group and transposition of the double bond from 4-5 to 5-6 (or 5-10); e) oxydation of the hydroxyl in 17 to a ketonic group; f) formation of a double bond in 15-16 by oxidation with Pd(II) acetate after transformation to sililenolether; g) ethynylation in position 17 with Li acetilide; h) hydrolysis of the acetalic group of position 3.

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