Gram Scale Total Synthesis of 2-Hydroxy-3-methylcarbazole, Pyrano[3,2-a]carbazole and Prenylcarbazole Alkaloids

被引：24

作者：

Dai, Jianxin ^{[1
]}

Ma, Dengke ^{[1
]}

Fu, Chunling ^{[1
]}

Ma, Shengming ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Zhejiang, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 25期

基金：

中国国家自然科学基金;

关键词：

Natural products; Alkaloids; Nitrogen heterocycles; Cyclization; Rearrangement; Allylation; TRANSITION-METAL-COMPLEXES; CARBAZOLE ALKALOIDS; ORGANIC-SYNTHESIS; MURRAYA-KOENIGII; EFFICIENT; GIRINIMBINE; BENZANNULATION; CONSTITUENTS;

D O I：

10.1002/ejoc.201500783

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Naturally occurring carbazole alkaloids including 2-hydroxy-3-methylcarbazole, pyrano[3,2-a]carbazole alkaloids (girinimbine and murrayacine) and prenylcarbazole alkaloids (mukoenine-A and heptaphylline) have been synthesized on gram scale. The key compound in these syntheses is 9-benzyl-2-methoxy-3-methylcarbazole, which was prepared by an efficient Au-catalyzed cyclization reaction of readily available methoxypropadiene and indole-2-carbaldehyde. Girinimbine and murrayacine were synthesized by a concise PhB(OH)(2)-mediated intermolecular cyclization with 3-methylbut-2-enal. Palladium-catalyzed allylation/Claisen rearrangement proved to be the best route to mukoenine-A and heptaphylline.

引用

页码：5655 / 5662

页数：8

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