MICROBIOLOGICAL DEGRADATION OF BILE ACIDS

VII. PARTIAL SYNTHESIS OF 3, 12-DIKETO.Δ^{4, 6}-CHOLADIENIC ACID AND ITS DERIVATIVES FROM CHOLIC ACID

Abstract

1. The identification of the dehydrobromination product of 3-keto-4_??_-bromo-7α, 12α-diacetoxycholanic acid with pyridine was attempted and it was shown that the product having the dienone grouping is 3-keto-12α-acetoxy-Δ^{4, 6}-choladienic acid and it is not in the structure of Δ^{4, 7}-3-ketone reported by Matsumoto (2).
2. The partial syntheses of 3, 12-diketo-Δ^{4, 6}-choladienie acid and its derivatives from cholic acid were described, and these compounds were used to confirm the structure of the various intermediates of cholic acid obtained through the action of S. gelaticus 1164.
The authors express their hearty thanks to Prof. T. Shimizu and Prof. S. Mizuhara for their interests on this study and their encouragements, and to Mr. Y. Matsui of Research Laboratory, Shionogi & Co., Ltd. for his help in measuring the infrared absorption spectra and for his valuable criticism.