Samarium(II)-mediated 4-exo-trig cyclization.: A stereocontrolled approach to the core of pestalotiopsin A

被引：70

作者：

Johnston, D ^{[1
]}

Francon, N ^{[1
]}

Edmonds, DJ ^{[1
]}

Procter, DJ ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 13期

关键词：

D O I：

10.1021/ol015976a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2001 / 2004

页数：4

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