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Publication 19  

  1. Total Synthesis of 16-Desmethylepothilone B, Epothilone B10, Epothilone F, and Related Side Chain Modified Epothilone B Analogues
    K. C. Nicolaou, D. Hepworth, N. P. King, M. R. V. Finlay, R. Scarpelli, M. M. A. Pereira, B. Bollbuck, A. Bigot, B. Werschkun, N. Winssinger
    Chem. Eur. J. 2000, 6, 2783-2800

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.

DOI: 10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B 

open archive unige:24509