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Org Biomol Chem. 2003 Jan 21;1(2):328-37.

The first synthetic studies on pestalotiopsin A. A stereocontrolled approach to the functionalised bicyclic core.

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1
Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, UK G12 8QQ.

Abstract

Pestalotiopsin A is a structurally unique, caryophyllene-type sesquiterpene which has shown immunosuppressive activity and cytotoxicity in preliminary assays. A stereocontrolled approach to the functionalised 2-oxabicyclo[3.2.0]-heptane core of pestalotiopsin A is described. This constitutes the first synthetic studies on pestalotiopsin A. Our approach includes a samarium(II)-mediated 4-exo-trig cyclisation and a trans-lactonisation process triggered by the addition of alkylytterbium reagents to a cyclobutanone intermediate. Further manipulation provides access to advanced intermediates which are excellent precursors for the future construction of the final ring of the target.

PMID:
12929428
[Indexed for MEDLINE]
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