Issue 2, 2003

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
17 Sep 2002
Accepted
11 Nov 2002
First published
13 Dec 2002

Org. Biomol. Chem., 2003,1, 328-337

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

D. Johnston, E. Couché, D. J. Edmonds, K. W. Muir and D. J. Procter, Org. Biomol. Chem., 2003, 1, 328 DOI: 10.1039/B209066J

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