Total synthesis of hypermodified epothilone analogs with potent in vitro antitumor activity

Kuzniewski, Christian N; Gertsch, Jürg; Wartmann, Markus; Altmann, Karl-Heinz (2008). Total synthesis of hypermodified epothilone analogs with potent in vitro antitumor activity. Organic letters, 10(6), pp. 1183-6. Washington, D.C.: American Chemical Society 10.1021/ol800089x

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The convergent total synthesis of hypermodified epothilone analogs 1 and 2 has been achieved with the stereoselective cyclopropanation of allylic alcohol 17 and ring-closing olefin metathesis with diene 22 as the key steps. In spite of significant structural differences between these analogs and the natural epothilone scaffold, 1 and 2 are potent inducers of tubulin polymerization and inhibit the growth of human cancer cells in vitro with sub-nM IC50 values.

Item Type:

Journal Article (Original Article)

Division/Institute:

04 Faculty of Medicine > Pre-clinic Human Medicine > Institute of Biochemistry and Molecular Medicine

UniBE Contributor:

Gertsch, Jürg

ISSN:

1523-7060

ISBN:

18303900

Publisher:

American Chemical Society

Language:

English

Submitter:

Factscience Import

Date Deposited:

04 Oct 2013 15:05

Last Modified:

04 May 2014 23:20

Publisher DOI:

10.1021/ol800089x

PubMed ID:

18303900

Web of Science ID:

000254032100037

URI:

https://boris.unibe.ch/id/eprint/28320 (FactScience: 120043)

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