Synthesis of Isoindolobenzazepine Alkaloids Based on Radical Reactions or Pd(0)-Catalyzed Reactions

被引：46

作者：

Onozaki, Yu ^{[1
]}

Kurono, Nobuhito ^{[1
]}

Senboku, Hisanori ^{[1
]}

Tokuda, Masao ^{[1
]}

Orito, Kazuhiko ^{[1
]}

机构：

[1] Hokkaido Univ, Organ Synth Lab, Div Mol Chem, Grad Sch Engn, Sapporo, Hokkaido 0608628, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 15期

关键词：

INTRAMOLECULAR HECK REACTION; CONVENIENT SYNTHESIS; TRANSLOCATION REACTIONS; NITROGEN-HETEROCYCLES; AROMATIC-SUBSTITUTION; RING-EXPANSION; ARYL HALIDES; SIMPLE ROUTE; LENNOXAMINE; CYCLIZATION;

D O I：

10.1021/jo900311g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methods for synthesis of a ring system characteristic of isoindolobenzazepine alkaloids were studied. Synthesis of lennoxamine and a formal synthesis of chelenine were accomplished in a short route via radical or Pd(0)-catalyzed cyclization as the key step. An altenative approach based on a radical migration of a cyano group or Pd(0)-catalyzed carbonylation was also developed for both alkaloids.

引用

页码：5486 / 5495

页数：10

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