Studies on the synthesis of cardiotonic steroids. I. Efficient synthesis of cardenolides.

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Abstract
Practical synthetic methods of natural cardenolides are illustrated in the syntheses of xysmalogenin and digitoxigenin. The new routes employ pregn-14-en-20-one as key intermediate which was prepared by partial reduction of 14,16-dien-20-one with triphenylstannane or triethylsilane. A general and efficient method was devised for obtaining cardenolides consisting of 21-methylsulfenylation of pregnen-20-one, the reaction of the resulting 21-methylthio derivative with bromoacetate and zinc, alumina chromatography of epoxy ester obtained from the S-methylated Reformatsky product.

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