Toward the improvement of the tandem halide displacement/amide coupling spiro-cyclization as a new route to γ-lactam and pyrroloisoquinoline templates

被引：28

作者：

Allous, Iyad ^{[1
]}

Comesse, Sebastien ^{[1
]}

Berkes, Dusan ^{[2
]}

Alkyat, Amar ^{[3
]}

Daich, Adam ^{[1
]}

机构：

[1] Univ Havre, CNRS, FR 3038, UFR Sci & Tech,URCOM,INC3M,EA 3221, F-76058 Le Havre, France

[2] Slovak Tech Univ, Dept Organ Chem, SK-81237 Bratislava, Slovakia

[3] Damascus Univ, Dept Pharmaceut Chem & Med Control, Damascus, Syria

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 31期

关键词：

Pentacyclic spiro-oxindoles; 5,5-Spiroimides; Spirocyclization; N-Acyliminium species; Alkaloids; ALDOSE REDUCTASE INHIBITORS; MAMMALIAN-CELL CYCLE; SPIROTRYPROSTATIN B; ALKALOIDS; DISCOVERY; POTENT; AGENTS;

D O I：

10.1016/j.tetlet.2009.02.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two efficient and rapid accesses to spiro-oxindole entities bearing an imide function were presented, and their performance was compared. The key components are N-substituted alpha-bromoacetamides to reach these derivatives in tandem process. The resulting spiro-imides from these methodologies were regioselectively reduced into corresponding N-acyliminium precursors, which were subsequently submitted to an intramolecular cyclization to provide pentacyclic spiro-oxindole architecture analogues to pteropodine and spirotryprostatin-B alkaloids with high diastereoselective control. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：4411 / 4415

页数：5

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