Synthesis of a simplified analogue of eleutherobin via a Claisen rearrangement and ring closing metathesis strategy

Gary C H Chiang; Andrew D Bond; Andrew Ayscough; Gilles Pain; Sylvie Ducki; Andrew B Holmes

doi:10.1039/b413426e

Synthesis of a simplified analogue of eleutherobin via a Claisen rearrangement and ring closing metathesis strategy

Chem Commun (Camb). 2005 Apr 14:(14):1860-2. doi: 10.1039/b413426e. Epub 2005 Feb 11.

Authors

Gary C H Chiang¹, Andrew D Bond, Andrew Ayscough, Gilles Pain, Sylvie Ducki, Andrew B Holmes

Affiliation

¹ Department of Chemistry, University of Cambridge, UK.

PMID: 15795767
DOI: 10.1039/b413426e

Abstract

The enantioselective synthesis of a simplified eleutherobin analogue by ring closing metathesis (RCM) of the 2,9-divinyl-substituted tetrahydro-oxonin is described; the analogue and an advanced intermediate revealed microtubule stabilising properties in the micromolar range.

Publication types

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

MeSH terms

Crystallography, X-Ray
Diterpenes / chemical synthesis
Diterpenes / chemistry*
Epoxy Compounds / chemistry
Models, Molecular
Molecular Structure

Substances

Diterpenes
Epoxy Compounds
eleutherobin