Synthesis of furan-bridged 10-membered rings through [8+2]-cycloaddition of dienylfurans and acetylenic esters

被引：18

作者：

Zhang, L ^{[1
]}

Wang, Y ^{[1
]}

Buckingham, C ^{[1
]}

Herndon, JW ^{[1
]}

机构：

[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 08期

关键词：

D O I：

10.1021/ol050416n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling of various dienylfurans with dimethyl acetylenedicarboxylate (DMAD) has been examined. In most cases this reaction proceeds via [8 + 2]-cycloaddition to afford furan-bridged 10-membered ring systems as a single diastereomer. Dienylfuran intermediates were generated using either a chromium carbene-based method or aldol-based methods. Reaction of [8 + 2]-cycloadducts with electrophilic reagents occurred selectively at the enol ether alkene.

引用

页码：1665 / 1667

页数：3

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