Synthesis of ent-alantrypinone

被引：63

作者：

Hart, DJ ^{[1
]}

Magomedov, NA ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2001年 / 123卷 / 25期

关键词：

D O I：

10.1021/ja010066+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This paper presents a synthesis of ent-alantrypinone (ent-6), the enantiomer of a natural product produced by the fungus Penicillium thymicola. The synthesis revolves around the Li[Me3AlSPh] -promoted isomerization of iminobenzoxazine 33 to quinazolinone 34, an N-acyliminium ion cyclization that converts enamide 9 to bridged indole 35, and rearrangement of 35 to oxindole ent-6, Ancillary chemistry that involves thermal fragmentation of an iminobenzoxazine to a nitrile ylide and Me2AlSPh-mediated cyclization of oxime ether-ester 22 to pyrrolidinone 23 is also described.

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页码：5892 / 5899

页数：8

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