Synthesis of furano[2,3-c]pyran-3-one and thieno[2,3-c]pyran-3-one derivatives through the coupling of 3-alkynyl-2-heteroaromatic carboxaldehydes with Fischer carbene complexes:: Total synthesis of a Baccharis-derived cadinene derivative

被引：44

作者：

Zhang, YS ^{[1
]}

Herndon, JW ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 12期

关键词：

D O I：

10.1021/jo011136y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling of Fischer carbene complexes with 3-alkynyl-2-heteroaromatic carboxaldehyde derivatives has been examined. The reaction affords pyrones fused to furans or thiophenes in a single step. The compounds are stable enough for isolation. If the carbene complex features a remote alkene substituent, a subsequent Diels-Alder reaction can occur. This reaction has been used as the key step in the synthesis of a naturally occurring cadinene derivative.

引用

页码：4177 / 4185

页数：9

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