Total synthesis of epothilone B.
[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.
Valluri
M
M
Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, P.O. Box 1848, University, Mississippi 38677-1848, USA.
Hindupur
R M
RM
Bijoy
P
P
Labadie
G
G
Jung
J C
JC
Avery
M A
MA
D000447:Aldehydes / Q000737:chemistry; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D034261:Epothilones; D007202:Indicators and Reagents; D018942:Macrolides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D000903:Antibiotics, Antineoplastic; D000935:Antifungal Agents; D034261:Epothilones; D007202:Indicators and Reagents; D018942:Macrolides; C093788:epothilone B