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Oxidative and reductive transformations of epothilone A
M Sefkow1, M Kiffe, D Schummer
1Gesellschaft für Biotechnologische Forschung mbH, Abt. Naturstoffchemie, Braunschweig, Germany. sefkow@rz.uni-potsdam.de
Bioorganic & Medicinal Chemistry Letters
|January 5, 1999
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.