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Derivatization of the C12-C13 functional groups of epothilones A, B and C
1Gesellschaft für Biotechnologische Forschung mbH, Abt. Naturstoffchemie, Germany. sefkow@rz.uni-potsdam.de
Bioorganic & Medicinal Chemistry Letters
|January 5, 1999
Abstract:
Epothilone A reacted with hydrohalic acids to C12-C13 halohydrin regioisomers (ratios: 2:1-4:1), whereas epothilone B gave under the same conditions the isomerically pure C12 halo C13 hydroxy derivative. With non-nucleophilic Brønstedt acids and with Lewis acids a highly solvent dependent product distribution and some unexpected rearrangement products were observed. Epothilone C bearing a double bond between C12 and C13 was regioselectively dihydroxylated or hydrogenated at that position.