The formal total synthesis of epothilone A

Authors
Kalesse, M Quitschalle, M Claus, E Gerlach, K Pahl, A Meyer, HH
Citation
M. Kalesse et al., The formal total synthesis of epothilone A, EUR J ORG C, (11), 1999, pp. 2817-2823
Citations number
48
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
11
Year of publication
1999
Pages
2817 - 2823
Database
ISI
SICI code
1434-193X(199911):11<2817:TFTSOE>2.0.ZU;2-2
Abstract
The formal total synthesis of epothilone A is described. The key steps in t he synthesis of the northern hemisphere are a Z-selective ten-membered ring -closing metathesis reaction (RCM) and the diastereoselective alkylation at C8. Aldehyde 3 is formed by introduction of the thiazole moiety by a Witti g reaction and subsequent functional group transformation. An efficient rou te to keto acid 5 is described.