Stereocontrolled assembly of tetrasubstituted tetrahydrofurans: A concise synthesis of virgatusin

被引：30

作者：

Akindele, T ^{[1
]}

Marsden, SP

Cumming, JG

机构：

[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England

[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 17期

关键词：

D O I：

10.1021/ol051292h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The condensation of substituted allylsiloxanes with aldehydes leads to the highly stereoselective construction of 2,3,4,5-tetrasubstituted tetrahydrofurans. With electron-rich aryl and alpha,beta-unsaturated aldehydes as substrates, the stereochemical outcome at C5 can be dictated by appropriate choice of Lewis acid. The reaction has been applied to a concise (nine step) synthesis of (+)-virgatusin (ent-1).

引用

页码：3685 / 3688

页数：4

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