Total syntheses of epothilones B and d.
A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization.
Jung
Jae-Chul
JC
Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, P.O. Box 1848, Mississippi 38677-1848, USA.
Kache
Rajashaker
R
Vines
Kimberly K
KK
Zheng
Yan-Song
YS
Bijoy
Panicker
P
Valluri
Muralikrishna
M
Avery
Mitchell A
MA
D034261:Epothilones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D034261:Epothilones; C114026:desoxyepothilone B; C093788:epothilone B