PARTIAL SYNTHESIS OF THE 2 3-ALPHA-7-ALPHA-12-ALPHA-TRIHYDROXYCOPROSTANIC ACIDS AND OF SIMILAR BILE ACIDS WITH EXTENDED SIDE CHAINS
PARTIAL SYNTHESIS OF THE 2 3-ALPHA-7-ALPHA-12-ALPHA-TRIHYDROXYCOPROSTANIC ACIDS AND OF SIMILAR BILE ACIDS WITH EXTENDED SIDE CHAINS
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DOI：
10.1042/bj0640593a
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发表时间：
1956-01-01
影响因子：
4.1
通讯作者：
BRIDGWATER, RJ
中科院分区：
文献类型：
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作者：
BRIDGWATER, RJ
采用Kolbe电解交叉偶联法合成了同胆酸、双胆酸、3[α]:7[α]:12[α]-三羟基-25-L-共前列腺酸和2 (25-Land 25-D)-3[α]:7[α]:12[α]-三羟基同前列腺酸，后两种化合物与L-和D-[β]-甲基戊二酸相关，因此与L-和D-甲基戊二酸相关。这两种（25-L和25-D）-3[α]:7[α]:12[α]-三羟基同质共前列腺酸通过Wieland-Barbier法降解为2种相应的（25-L和25-D）-3[α]:7[α]:12[α]-三羟基共前列腺酸。后两种酸与两种天然存在的3[α]:7[α]:12[α]-三羟基前列腺酸-26-酸（日语分别为“[α]-”和“[β]-”三羟基前列腺酸）相同，这两种酸是从不同物种的胆汁中分离出来的。体内由胆固醇中的甲基氧化生成胆汁醇或胆汁酸形成的新的不对称中心可以被认为是非特异性的，因为这两种光学异构体都得到了。
The Kolbe electrolytic cross-coupling synthesis was used to synthesize homocholic, bishomocholic, 3[alpha]:7[alpha]:12[alpha]-tri-hydroxy-25-L-coprostanic and two (25-Land 25-D)-3[alpha]:7[alpha]:12[alpha]-trihydroxyhomocoprostanic acids, the latter 2 compounds being thus related to L- and D-[beta]-methylglutaric acids and hence to L- and D-glyceraldehyde. The two (25-L and 25-D)-3[alpha]:7[alpha]:12[alpha]-trihydroxyhomo-coprostanic acids were degraded by the Wieland-Barbier method into the 2 corresponding (25-L and 25-D)-3[alpha]:7[alpha]:12[alpha]-trihydroxycoprostanic acids. These latter 2 acids were identical with the 2 naturally occurring 3[alpha]:7[alpha]:12[alpha]-trihydroxycoprostan-26-oic acids (Japanese "[alpha]-" and "[beta]-" trihydroxycoprostanic acids respectively), which were isolated from the biles of various species. The formation of a new asymmetric center by the oxidation in vivo of a methyl group in cholesterol to give bile alcohols or bile acids may be considered to be non-specific, in the sense that both optical isomers are obtained.