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

Derek Johnston; Emmanuel Couché; David J. Edmonds; Kenneth W. Muir; David J. Procter

doi:10.1039/b209066j

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

Derek Johnston, Emmanuel Couché, David J. Edmonds, Kenneth W. Muir, David J. Procter

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	328-337
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	1
Issue number	2
DOIs	https://doi.org/10.1039/b209066j
Publication status	Published - 21 Jan 2003

Keywords

Addition reaction (nucleophilic; prepn. of the functionalized bicyclic core of pestalotiopsin A from a cyclofuranone via a samarium(II)-mediated 4-exo-trig cyclization and a trans-lactonization process initiated by a nucleophilic addn.); Crystal structure; Molecular structure (of a functionalized bicyclic core of pestalotiopsin A); Lactonization; Stereoselective synthesis (prepn. of the functionalized bicyclic core of pestalotiopsin A from a cyclofuranone via a samarium(II)-mediated 4-exo-trig cyclization and a trans-lactonization process initiated by a nucleophilic addn.); Cyclization (stereoselective; prepn. of the functionalized bicyclic core of pestalotiopsin A from a cyclofuranone via a samarium(II)-mediated 4-exo-trig cyclization and a trans-lactonization process initiated by a nucleophilic addn.)

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10.1039/b209066j

CCDC 194435: Experimental Crystal Structure Determination
Johnston, D. (Contributor), Couché, E. (Contributor), Edmonds, D. J. (Contributor), Muir, K. W. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2003
DOI: 10.5517/cc6jb34, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc6jb34&sid=DataCite
Dataset

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title = "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.",

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year = "2003",

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AB - 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.

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DO - 10.1039/b209066j

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JF - Organic and Biomolecular Chemistry

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ER -

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

Abstract

Keywords

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CCDC 194435: Experimental Crystal Structure Determination

Cite this