Universität Tübingen
Ein neuer Syntheseweg zu Epothilon-Analoga und ein effizienter Zugang zu Cyclohexenylaminen als Vorstufen in der Totalsynthese von Epibatidin
Abstract
Epothilones are macrolides showing microtubules stabilizing activity comparable to this of Taxol®. Therefore, they are attractive targets for analogue design. The described novel strategy for generation of epothilone analogues utilizes a WITTIG reaction for formation of the C8-C15 fragment, a stereoselective EVANS aldol reaction to establish the C7-C8 bond, and a YAMAGUCHI macrolactonization for the ring closure. Additionally, a synthesis of substituted cyclohexenylamines by ring closing metathesis applying a GRUBBS catalyst is described. This method is a useful alternative to the DIELS-ALDER strategy. In general, such cyclohexenes are of interest for the synthesis of bicyclic heterocycles by transannular reactions and are used as precursors in the synthesis of the natural alkaloid epibatidine.
Author and committee
dc:creator, dc:contributor.*- Author
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- Marquardt, Tzvetelina
Identifiers
dc:identifier.*- Identifier
- hdl:10900/48353