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Paper | Regular issue | Vol 41, No. 9, 1995, pp.2027-2032
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7149
Preparation of 15-Hydroxy-Δ13,14-milbemycin A4 and Its Transformation to 13-Alkylmilbemycins

Satoru Naito, Makio Kobayashi, and Akio Saito

*Medicinal Chemistry Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140, Japan

Abstract

13-Alkylmilbemycins were synthesized regiospecifically by Claisen rearrangement of a 15-hydroxy-Δ13,14-milbemycin derivative, which was prepared selectively from a 14,15-epoxymilbemycin derivative by isomerization of the 14,15-epoxide moiety induced by ethylaluminum bis(2,6-diphenylphenoxide).