Total synthesis of 16-desmethylepothilone B, epothilone B10, epothilone F, and related side chain modified epothilone B analogues.
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.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA. kcn@scripps.edu
Hepworth
D
D
King
N P
NP
Finlay
M R
MR
Scarpelli
R
R
Pereira
M M
MM
Bollbuck
B
B
Bigot
A
A
Werschkun
B
B
Winssinger
N
N
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*
D000970:Antineoplastic Agents; D034261:Epothilones; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D013844:Thiazoles; C093788:epothilone B