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Abstract
An efficient method for the oxyfunctionalization at C-1 in 5β-steroid (A/B-cis) is described as exemplified by conversion of lithocholic acid (3α-hydroxy-5β-cholan-24-oic acid) to 1β,3α-dihydroxy-5β-cholan-24-oic acid. The key reactions used are regioselective functionalization at C-2 in the 5β-steroid nucleus, stereoselective epoxidation of intermediary α,β-conjugated ketone with dimethyldioxirane, and subsequent reductive cleavage of the resulting β-epoxy-ketone with PhSeNa.
ACKNOWLEDGMENTS
This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture of Japan. Masami Kitamura and Masako Ishibashi contributed able technical assistance.