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Paper | Regular issue | Vol 63, No. 6, 2004, pp.1335-1343
Published online, 30th March, 2004
DOI: 10.3987/COM-04-10053
Regioselective Cleavage of Trisubstituted Epoxy-Linkage Using Lithium Trialkylborohydride Reagents: A New Route to the Key Intermediate of Maxacalcitol

Hitoshi Shimizu,* Kazuki Shimizu, Noboru Kubodera, Kenichi Yakushijin, and David A. Horne

*Chugai Pharmaceutical Company, Ltd., 5-5-1, Ukima, Kita-ku, Tokyo 115-8543, Japan

Abstract

Optimal conditions for the reductive cleavage of a trisubstituted epoxide leading regioselectively to the key intermediate tertiary alcohol of Maxacalcitol, used for the treatment of secondary hyperparathyroidism and psoriasis, have been established using lithium tri(sec-butyl)borohydride (L-Selectride) in THF.