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Chapter 6,376

Seco steroids 10. synthesis of c homo 11 12 seco estradiol/

Lal, K.; Kole, P.L.; Ray, S.

Indian Journal of Chemistry. Sect. B 22(3): 220-224

1983

ISSN/ISBN: 0376-4699
Accession: 006375550
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C-Homo-11,12-secoestradiol (1) and its derivatives have been synthesized starting from 17.beta.-acetoxy-3-methoxy-9-oxo-9,11-secoestra-1,3,5(10)-trien-11-oic acid (2). Treatment of 2 with CH3MgI under controlled conditions gives methyl 17.beta.-hydroxy-3-methoxy-C-homo-11,12-secoestra-1,3,5(10), 8(9)-tetraene-12-carboxylate (5), which is converted into 17.beta.-hydroxy-3-methoxy-C-homo-11,12-secoestra-1,3,5(10), 8(9)-tetraene (10) through a sequence of reactions. The 10 is also prepared starting from 9,11-secoestradiol-3-methyl ether. The 10 on Birch reduction followed by demethylation under alkaline conditions yields 1. Pyridinium chlorochromate oxidation of 10 gives 3-methoxy-C-homo-11,12-secoestra-1,3,5(10),8(9)-tetraen-17-one (15), while LAH reduction of 5 leads to 3-methoxy-C-homo-11,12-secoestra-1,3,5(10),8(9)-tetraene-12,17.beta.-diol (16).

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