Derivatization of the C12-C13 functional groups of epothilones A, B and C.
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.
Sefkow
M
M
Gesellschaft für Biotechnologische Forschung mbH, Abt. Naturstoffchemie, Germany. sefkow@rz.uni-potsdam.de
Kiffe
M
M
Höfle
G
G
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D034261:Epothilones; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D000970:Antineoplastic Agents; D034261:Epothilones; D004852:Epoxy Compounds; D013844:Thiazoles; C093787:epothilone A; C093788:epothilone B