Total synthesis of (±)-alantrypinone by hetero Diels-Alder reaction

被引：51

作者：

Chen, ZC ^{[1
]}

Fan, JF ^{[1
]}

Kende, AS ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 01期

关键词：

D O I：

10.1021/jo030273n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient total synthesis of (+/-)-alantrypinone 4 by hetero Diels-Alder reaction of a novel pyrazine diene 9 with either a functionalized 3-alkylideneoxindole or 3-methyleneoxindole itself is described. The Diels-Alder reactions provide both the desired regiochemistry and exo selectivity. An interesting anionic equilibration between alantrypinone 4 and its epimer 31 or between its ester analogues 23 and 24 has been demonstrated, and a mechanism has been proposed.

引用

页码：79 / 85

页数：7

共 31 条

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