Lactol-Ene Reaction: An Efficient Access to the Synthesis of 22R,  25-Dihydroxy Steroid Side Chains

Koichi Mikami; Hiroyuki Kishino; Hiroyuki Matsueda; Teck-Peng Loh

doi:10.1055/s-1993-22504

Synlett 1993; 1993(7): 497-498
DOI: 10.1055/s-1993-22504

letter

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Lactol-Ene Reaction: An Efficient Access to the Synthesis of 22R, 25-Dihydroxy Steroid Side Chains

Koichi Mikami^* , Hiroyuki Kishino, Hiroyuki Matsueda, Teck-Peng Loh

^*Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan

Abstract

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Lewis acid-promoted carbonyl-ene reaction of steroidal olefin with a new type of enophile, γ-lactol is shown to exhibit high levels of α-diastereofacial selectivity and 20S, 22R-anti diastereoselectivity to afford 22R, 25-dihydroxy steroid side chains featuring insect moulting steroidal hormones, ecdysones and marine steroid, depresosterol.

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