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filingDate 1992-11-27-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_725c2c24cc76e9b1fddb05c4d417cac8
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publicationDate 1994-06-01-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber DE-4239946-A1
titleOfInvention Estrane derivatives with a 14alpha, 15alpha-methylene group and process for their preparation
abstract Prepn. of 14alpha,15alpha-methylene-estrane derivs. of formula (Ia)-(Id) comprises: (a) methylenating a 3-alkoxy-estra-1,3,5(10),8,14-pentaen-17alpha-ol of formula (II); (b) oxidising the resulting 3-alkoxy-14alpha,15alpha-methylene-estra-1,3,5(10) 8-tetraen-17-alpha-ol of formula (III); (c) reducing the 3-alkoxy-17-oxo-14alpha,15alpha-methylene-estra-1,3,5(10),8-tetraene of formula (IV) obtd.; and opt. subjecting the resulting 3-alkoxy-14alpha,15alpha-methylene-estra-1,3,5(10),8-tetraen-17beta-ol of formula (Ia) to (d) ether cleavage to give 14alpha,15alpha-methylene-estra-1,3,5(10),8-tetraene-3,17beta-diol of formula (Ib); or e) redn. to a 3-alkoxy-14alpha,15alpha-methylene-estra-1,3,5(10)-trien-17beta-ol of formula (Ic) followed by ether cleavage of the latter to 14alpha,15alpha-methylene-estra-1,3,5(10)-triene-3,17beta-diol of formula (Id). R = lower alkyl. (Ia), (Ib) and (IV) are new. (Ic) and (Id) are described in DD 145919. USE/ADVANTAGE - (Ia)-(Id) and (IV) are anti-fertility agents. The method is more effective and cheaper for the prodn. of (Ic) and (Id) than that described in DD 145919, esp. as fewer steps are required.
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