Stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants

Schiess, Raphael; Gertsch, Jürg; Schweizer, W Bernd; Altmann, Karl-Heinz (2011). Stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants. Organic letters, 13(6), pp. 1436-9. Washington, D.C.: American Chemical Society 10.1021/ol200114k

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A general strategy has been devised for the stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants thereof, which relies on late stage introduction of the heterocycle through Wittig olefination of ketone 14. Formation of the macrocycle was achieved through RCM-based ring closure and introduction of the cyclopropane moiety involved a highly selective Charette cyclopropanation of allylic alcohol 7.

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 14:23

Last Modified:

17 Mar 2015 21:03

Publisher DOI:

10.1021/ol200114k

PubMed ID:

21338105

Web of Science ID:

000288148800044

URI:

https://boris.unibe.ch/id/eprint/8162 (FactScience: 213650)

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