title: Total syntheses of epothilones B and d.
abstract: 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.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, P.O. Box 1848, Mississippi 38677-1848, USA.
authors.forename: Jae-Chul
authors.initials: JC
authors.lastname: Jung
authors.forename: Rajashaker
authors.initials: R
authors.lastname: Kache
authors.forename: Kimberly K
authors.initials: KK
authors.lastname: Vines
authors.forename: Yan-Song
authors.initials: YS
authors.lastname: Zheng
authors.forename: Panicker
authors.initials: P
authors.lastname: Bijoy
authors.forename: Muralikrishna
authors.initials: M
authors.lastname: Valluri
authors.forename: Mitchell A
authors.initials: MA
authors.lastname: Avery
mesh_terms: D034261:Epothilones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
chemical_list: D034261:Epothilones; C114026:desoxyepothilone B; C093788:epothilone B