Synthesis of 10. beta.-oxiranyl and 10. beta.-thiiranyl steroids

…, PS Furth, MJ Shih, CH Robinson

Index: Childers; Furth; Shih; Robinson Journal of Organic Chemistry, 1988 , vol. 53, # 25 p. 5947 - 5951

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Citation Number: 19

Abstract

7a and 7b with TPS-trifluoroacetic acid gave, respectively,(19R)-and (19S)-5, 19- (thiomethylene)-19-(trifluoroacetoxy)-5j3-androstane-3, 17-dione (9a and 9b) through internal trapping of a reaction intermediate. Hydrolysis of 9a and 9b gave, respectively, the corresponding 19-hydroxy heterocycles, 10a and lob, which could also be obtained by reaction of oxiranes 7a and 7b with TPS-methanesulfonic acid. The reactions involving ...