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 Finlay; R Scarpelli; M M Pereira; B Bollbuck; A Bigot; B Werschkun; N Winssinger

doi:10.1002/1521-3765(20000804)6:15<2783::aid-chem2783>3.0.co;2-b

Total synthesis of 16-desmethylepothilone B, epothilone B10, epothilone F, and related side chain modified epothilone B analogues

Chemistry. 2000 Aug 4;6(15):2783-800. doi: 10.1002/1521-3765(20000804)6:15<2783::aid-chem2783>3.0.co;2-b.

Authors

K C Nicolaou¹, D Hepworth, N P King, M R Finlay, R Scarpelli, M M Pereira, B Bollbuck, A Bigot, B Werschkun, N Winssinger

Affiliation

¹ Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA. kcn@scripps.edu

PMID: 10985727
DOI: 10.1002/1521-3765(20000804)6:15<2783::aid-chem2783>3.0.co;2-b

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Epothilones*
Epoxy Compounds / chemical synthesis*
Epoxy Compounds / chemistry*
Indicators and Reagents
Molecular Conformation
Molecular Structure
Structure-Activity Relationship
Thiazoles / chemical synthesis*
Thiazoles / chemistry*

Substances

Antineoplastic Agents
Epothilones
Epoxy Compounds
Indicators and Reagents
Thiazoles
epothilone B