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Issue 2, 2003
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The first synthetic studies on pestalotiopsin A. A stereocontrolled approach to the functionalised bicyclic core

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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

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Supplementary files

Article information


Submitted
17 Sep 2002
Accepted
11 Nov 2002
First published
13 Dec 2002

Org. Biomol. Chem., 2003,1, 328-337
Article type
Paper

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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