title: Total synthesis of 16-desmethylepothilone B, epothilone B10, epothilone F, and related side chain modified epothilone B analogues.
abstract: The macrolactonization-based strategy for the total synthesis of epothilones has been streamlined and improved to a high level of efficiency and stereoselectivity. This strategy has been applied to the construction of vinyl iodide 19 which served as a common intermediate for the synthesis of a series of natural and designed epothilones including an epothilone B10 (3), epothilone F (5), 16-desmethylepothilone B (14), pyridine epothilones 57a-57g, dimeric epothilones 59 and 61, and benzenoid epothilones 63a-63g.
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA. kcn@scripps.edu
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: D
authors.initials: D
authors.lastname: Hepworth
authors.forename: N P
authors.initials: NP
authors.lastname: King
authors.forename: M R
authors.initials: MR
authors.lastname: Finlay
authors.forename: R
authors.initials: R
authors.lastname: Scarpelli
authors.forename: M M
authors.initials: MM
authors.lastname: Pereira
authors.forename: B
authors.initials: B
authors.lastname: Bollbuck
authors.forename: A
authors.initials: A
authors.lastname: Bigot
authors.forename: B
authors.initials: B
authors.lastname: Werschkun
authors.forename: N
authors.initials: N
authors.lastname: Winssinger
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D034261:Epothilones; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D034261:Epothilones; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D013844:Thiazoles; C093788:epothilone B