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 (1) 21-methylsulfenylation of pregnen-20-one, (2) the reaction of the resulting 21-methylthio derivative with bromoacetate and zinc, (3) alumina chromatography of epoxy ester obtained from the S-methylated Reformatsky product.
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