Oxidative and reductive transformations of epothilone A.

M Sefkow; M Kiffe; D Schummer; G Höfle

doi:10.1016/s0960-894x(98)00545-9

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Oxidative and reductive transformations of epothilone A.

M Sefkow·M Kiffe·D Schummer·G Höfle

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Abstract

The C7 hydroxy group of cytotoxic epothilone A was selectively oxidized using PDC. A selective oxidation of the C3 hydroxy group was accomplished with Me2S/(PhCO2)2 after in situ protection of C7-OH. Reduction of epothilone A or of a C5, C7 dioxo derivative with NaBH4 proceeded at the C5 carbonyl group. Oxidation and hydrogenation of the C16-C17 double bond proved to be difficult but it was easily cleaved with ozone and the resulting keto derivative was transformed to epothilone analogs with different side chains.

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Antineoplastic Agents Epothilones Epoxy Compounds Fermentation Oxidation-Reduction Thiazoles Journal Article

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M Sefkow, M Kiffe, D Schummer, G Höfle. 1998-11-03. Oxidative and reductive transformations of epothilone A.. https://doi.org/10.1016/s0960-894x(98)00545-9

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