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The total synthesis and anti-fertility activity of 6-silasteroids

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dc.contributor.author Pitt, Colin en_US
dc.contributor.author Friedman, Alan en_US
dc.contributor.author Rector, Douglas en_US
dc.contributor.author Wani, Mansukh en_US
dc.date.accessioned 2006-08-18T16:25:42Z en_US
dc.date.available 2006-08-18T16:25:42Z en_US
dc.date.issued 1975 en_US
dc.identifier.citation Tetrahedron 31N19 (1975) 2369-2377 en_US
dc.identifier.issn 0040-4020 en_US
dc.identifier.uri http://hdl.handle.net/1850/2308 en_US
dc.description.abstract 4,4-Dimethyl-6-methoxy-4-sila-1-tetralone (2) was prepared by a modified literature procedure and converted to 3-methoxy-6,6-dimethyl-6-silaestra-1,3,5(10),8,14-pentaen-17β-yl acetate (5c). Catalytic hydrogenation of 5c gave 3-methoxy-6,6-dimethyl-6-silaestra-1,3,5(10),8-tetraen-17β-yl acetate (6b), and its 14-iso- and Δ1,3,5(10),8(14) isomers, the proportions varying with the catalyst and solvent. Reduction of 6b with lithium-liquid ammonia, and O-demethylation, gave 6,6-dimethyl-6-silaestradiol (8b). Reduction of the 3-methyl ether of 8b with lithium-liquid ammonia-t-butanol and hydrolysis afforded 3-keto-6,6-dimethyl-6-silaestr-1(10)-en-17β-ol (15), which was catalytically reduced to its 1,10α-dihydro derivative 17. The 5,6 Si---C bond of 8b, 15 and their derivatives was cleaved by boron tribromide, aq. ethanolic hydrogen fluoride, and other reagents, providing a series of 5,6-seco-6,6-dimethyl-6-silasteroids. X-ray crystallographic analysis of 17 and the 17α-ethynyl derivative of 15 confirmed the stereochemical assignments. None of the compounds which were subjected to uterotropic, anti-uterotropic, or post-coital assays, showed significant activity. A partially completed synthesis of 6-silaestradiol (21a) is described. en_US
dc.format.extent 37365 bytes en_US
dc.format.mimetype application/pdf en_US
dc.language.iso en_US en_US
dc.publisher Elsevier: Tetrahedron en_US
dc.title The total synthesis and anti-fertility activity of 6-silasteroids en_US
dc.type Article en_US
dc.subject.keyword Catalysts en_US
dc.subject.keyword Reduction en_US
dc.subject.keyword Synthesis en_US
dc.identifier.url http://dx.doi.org/10.1016/0040-4020(75)80241-9

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