Total synthesis of epothilone B

M Valluri; R M Hindupur; P Bijoy; G Labadie; J C Jung; M A Avery

doi:10.1021/ol016173q

Total synthesis of epothilone B

Org Lett. 2001 Nov 15;3(23):3607-9. doi: 10.1021/ol016173q.

Authors

M Valluri¹, R M Hindupur, P Bijoy, G Labadie, J C Jung, M A Avery

Affiliation

¹ Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, P.O. Box 1848, University, Mississippi 38677-1848, USA.

PMID: 11700093
DOI: 10.1021/ol016173q

Abstract

[structure-see text] A convergent and stereoselective total synthesis of epothilone B (2) is described. The key steps are Normant reaction, Wadsworth-Emmons reaction of a methyl ketone 14 with the phosphonate reagent 7, diastereoselective aldol condensation of aldehyde 3 with enolate 4 to form the C6-C7 bond, and macrolactonization.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry
Antibiotics, Antineoplastic / chemical synthesis*
Antifungal Agents / chemical synthesis*
Epothilones*
Indicators and Reagents
Macrolides / chemical synthesis*
Stereoisomerism

Substances

Aldehydes
Antibiotics, Antineoplastic
Antifungal Agents
Epothilones
Indicators and Reagents
Macrolides
epothilone B