Synthesis of (-)-dactylolide and 13-desmethylene-(-)-dactylolide and their effects on tubulin

Zurwerra, Didier; Gertsch, Jürg; Altmann, Karl-Heinz (2010). Synthesis of (-)-dactylolide and 13-desmethylene-(-)-dactylolide and their effects on tubulin. Organic letters, 12(10), pp. 2302-5. Washington, D.C.: American Chemical Society 10.1021/ol100665m

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An efficient new synthesis has been elaborated for non-natural (-)-dactylolide ((-)-2) and its 13-desmethylene analogue 4, employing a HWE-based macrocyclization approach with beta-keto-phosphonate/aldehyde 19 and the respective 13-desmethylene derivative as the key intermediates. Both (-)-2 and 4 as well as the corresponding C20 alcohols inhibit human cancer cell proliferation with IC(50) values in the sub-micromolar range and induce the polymerization of tubulin in vitro.

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

Publisher:

American Chemical Society

Language:

English

Submitter:

Factscience Import

Date Deposited:

04 Oct 2013 14:12

Last Modified:

17 Mar 2015 19:14

Publisher DOI:

10.1021/ol100665m

PubMed ID:

20415434

Web of Science ID:

000277531000034

URI:

https://boris.unibe.ch/id/eprint/2439 (FactScience: 204938)

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