Intramolecular [4+3] cycloadditions. Towards a synthesis of widdrol

被引：24

作者：

Harmata, M ^{[1
]}

Kahraman, M ^{[1
]}

Adenu, G ^{[1
]}

Barnes, CL ^{[1
]}

机构：

[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA

来源：

HETEROCYCLES | 2004年 / 62卷

关键词：

cycloaddition; synthesis; thionium ion; furan; carbocation;

D O I：

10.3987/COM-03-S(P)53

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Certain substituted alkoxyallylic sulfones were alkylated and treated with Lewis acids to produce vinylthionium ions that underwent intramolecular [4+3] cycloaddition reactions with a tethered furan. Manipulation of the cycloadduct led to the synthesis of widdrol. Other attempts to prepare the cycloadducts were made, but none were exceptionally better than the route using vinylthionium ions as intermediates. Interesting aspects of the alkylation chemistry of phenylthio-substituted alkoxyallylic sulfones are detailed as well.

引用

页码：583 / 618

页数：36

共 66 条

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