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 serie...

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Bibliographic Details
Published in:Chemistry : a European journal 2000-08, Vol.6 (15), p.2783-2800
Main Authors: Nicolaou, K. C., Hepworth, David, King, N. Paul, Finlay, M. Raymond V., Scarpelli, Rita, Pereira, M. Manuela A., Bollbuck, Birgit, Bigot, Antony, Werschkun, Barbara, Winssinger, Nicolas
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
antitumor agents
designed analogues
epothilone
Epothilones
Epoxy Compounds - chemical synthesis
Epoxy Compounds - chemistry
Indicators and Reagents
Molecular Conformation
Molecular Structure
Structure-Activity Relationship
Thiazoles - chemical synthesis
Thiazoles - chemistry
total synthesis
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Summary: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 57 a–57 g, dimeric epothilones 59 and 61, and benzenoid epothilones 63 a–63 g.
ISSN:0947-6539
1521-3765
DOI:10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B