The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
MILBEMYCIN DERIVATIVES: EPOXIDATION OF MILBEMYCINS
SATORU NAITOAKIO SAITOYOUJI FURUKAWATADASHI HATAYASUO NAKADASHIGEKI MURAMATSUJUNYA IDE
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1994 Volume 47 Issue 7 Pages 812-820

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Abstract

Epoxidation reactions (MCPBA epoxidation and Sharpless epoxidation) were examined as a means of chemically modifying milbemycins as part of our program for discovering anthelmintics. 8, 9-Epoxy-, 14, 15-epoxy-, 8, 9-14, 15-diepoxy-, and 3, 4-8, 9-14, 15-triepoxymilbemycin A4 were se-lectively obtained from milbemycin A4 and its derivatives, in which either the C-5 and C-7 hydroxyl groups or C-5 alone were protected as appropriate by a silyl ether (in the former case) or a carbonyl group. Further silylation or epoxidation on these epoxidized compounds indicated that the configuration of each epoxide moiety of the mono- and diepoxides is in accord with that of the corresponding epoxide moiety of the triepoxide. Furthermore, in order to confirm the absolute configurations of these epoxide functionalities, an X-ray analysis of a carbamate derivative from the triepoxymilbemycin was conducted.

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