Abstract
The authors carry out the syntheses of 8a, 14a- and 8b, 14bepoxy-12-ketocholanic acids and their 3-acyl derivatives. B-Epoxides, by the action of proton acids and Lewis acids, are converted to the 7,14 choladienes, and by the action of boron trifluoride in acetic anhydride, to the product acylated at C/sup 11/, a-epoxides under proton acid conditions yield 8,14-dienes, and under backbone rearrangement conditions with boron trifluoride in benzene, to the rearrangement product, the methyl ester of 3a-methoxycarbonyloxy-5b-chola-9(11), 13(17)-diene14EPSILON-methyl-12-on-24-oic acid. The ..delta.. 13(17) bond was reduced by hydrogenation over Adams catalyst.
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