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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 8
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Original Articles

1β-HYDROXYLATION IN 5β-STEROIDS: AN EFFICIENT SYNTHESIS OF 1β,3α-DIHYDROXY-5β-CHOLAN-24-OIC ACID

Takeru Yamaguchi College of Humanities and Sciences, Nihon University, Setagaya, Sakurajosui, Tokyo, 156-8550, Japan
,
Ryusei Nakamori College of Humanities and Sciences, Nihon University, Setagaya, Sakurajosui, Tokyo, 156-8550, Japan
,
Takashi Iida College of Humanities and Sciences, Nihon University, Setagaya, Sakurajosui, Tokyo, 156-8550, Japan
&
Toshio Nambara Hoshi University, Shinagawa, Ebara, Tokyo, 140-1165, Japan
Pages 1213-1219 | Received 15 May 2000, Published online: 09 Nov 2006
 
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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.

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