Samarium(II)-Mediated 4-exo-trig Cyclization. A Stereocontrolled Approach to the Core of Pestalotiopsin A

Derek Johnston; Nicolas Francon; David J. Edmonds; David J. Procter

doi:10.1021/ol015976a

Samarium(II)-Mediated 4-exo-trig Cyclization. A Stereocontrolled Approach to the Core of Pestalotiopsin A

Derek Johnston, Nicolas Francon, David J. Edmonds, David J. Procter

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

Abstract

(Formula Presented) Pestalotiopsin A is a structurally unique caryophyllene-type sesquiterpene which has shown immunosuppressive activity and cytotoxicity in preliminary assays. A stereocontrolled approach to the functionalized 2-oxabicyclo[3.2.0]heptane core of pestalotiopsin A is described. The approach includes a samarium(II)-mediated 4-exo-trig cyclization and a trans-lactonization process triggered by the addition of alkylytterbium reagents to a cyclobutanone intermediate. † Socrates-Erasmus exchange student from the University of Marseille.

Original language	English
Pages (from-to)	2001-2004
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	13
DOIs	https://doi.org/10.1021/ol015976a
Publication status	Published - 28 Jun 2001

Keywords

Crystal structure; Molecular structure (of oxabicycloheptane deriv.); Cyclization (stereocontrolled prepn. of pestalotiopsin A oxabicycloheptane core via samarium(II)-mediated 4-exo-trig cyclization)

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10.1021/ol015976a

CCDC 164157: Experimental Crystal Structure Determination
Johnston, D. (Contributor), Francon, N. (Contributor), Edmonds, D. J. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2001
DOI: 10.5517/cc5htdv, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc5htdv&sid=DataCite
Dataset

Cite this

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title = "Samarium(II)-Mediated 4-exo-trig Cyclization. A Stereocontrolled Approach to the Core of Pestalotiopsin A",

abstract = "(Formula Presented) Pestalotiopsin A is a structurally unique caryophyllene-type sesquiterpene which has shown immunosuppressive activity and cytotoxicity in preliminary assays. A stereocontrolled approach to the functionalized 2-oxabicyclo[3.2.0]heptane core of pestalotiopsin A is described. The approach includes a samarium(II)-mediated 4-exo-trig cyclization and a trans-lactonization process triggered by the addition of alkylytterbium reagents to a cyclobutanone intermediate. † Socrates-Erasmus exchange student from the University of Marseille.",

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author = "Derek Johnston and Nicolas Francon and Edmonds, {David J.} and Procter, {David J.}",

year = "2001",

month = jun,

day = "28",

doi = "10.1021/ol015976a",

language = "English",

volume = "3",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Samarium(II)-Mediated 4-exo-trig Cyclization. A Stereocontrolled Approach to the Core of Pestalotiopsin A

AU - Johnston, Derek

AU - Francon, Nicolas

AU - Edmonds, David J.

AU - Procter, David J.

PY - 2001/6/28

Y1 - 2001/6/28

N2 - (Formula Presented) Pestalotiopsin A is a structurally unique caryophyllene-type sesquiterpene which has shown immunosuppressive activity and cytotoxicity in preliminary assays. A stereocontrolled approach to the functionalized 2-oxabicyclo[3.2.0]heptane core of pestalotiopsin A is described. The approach includes a samarium(II)-mediated 4-exo-trig cyclization and a trans-lactonization process triggered by the addition of alkylytterbium reagents to a cyclobutanone intermediate. † Socrates-Erasmus exchange student from the University of Marseille.

AB - (Formula Presented) Pestalotiopsin A is a structurally unique caryophyllene-type sesquiterpene which has shown immunosuppressive activity and cytotoxicity in preliminary assays. A stereocontrolled approach to the functionalized 2-oxabicyclo[3.2.0]heptane core of pestalotiopsin A is described. The approach includes a samarium(II)-mediated 4-exo-trig cyclization and a trans-lactonization process triggered by the addition of alkylytterbium reagents to a cyclobutanone intermediate. † Socrates-Erasmus exchange student from the University of Marseille.

KW - Crystal structure; Molecular structure (of oxabicycloheptane deriv.); Cyclization (stereocontrolled prepn. of pestalotiopsin A oxabicycloheptane core via samarium(II)-mediated 4-exo-trig cyclization)

U2 - 10.1021/ol015976a

DO - 10.1021/ol015976a

M3 - Article

SN - 1523-7052

VL - 3

SP - 2001

EP - 2004

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Samarium(II)-Mediated 4-exo-trig Cyclization. A Stereocontrolled Approach to the Core of Pestalotiopsin A

Abstract

Keywords

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Datasets

CCDC 164157: Experimental Crystal Structure Determination

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