1,185,449. Substituted estra-1,3,5(10)-triene- 3,11#,17#-triols. G. D. SEARLE & CO. 19 June, 1968 [21 June, 1967], No. 29212/68. Heading C2U. Novel steroids of the formula (wherein A is C 1-5 alkylene, ethynylene or vinylene; and R and RSP1/SP are each H or C 1-7 alkanoyl) are prepared from 3,11#-dihydroxyestra- 1,3,5(10) -trien-17-one and organometallic reagents. Thus, the 17α-phenylethynyl compound is prepared by using, for example, sodium phenyl acetylide, and the 17α-phenylalkyl compounds by using phenylalkyl zinc or magnesium halides followed by hydrolysis. The 17α-phenylvinyl compound is prepared by controlled hydrogenation of the 17α-phenyl ethynyl compound, and may be further hydrogenated to the 17α-phenylethyl compound. The acylates are prepared by acylation of the triols, the 3-monoacylates being the initial products and the 3,11-diacylates the products of more prolonged acylation.
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