Synthesis of the Pyrano[3,2-a]carbazole Alkaloids Koenine, Koenimbine, Koenigine, Koenigicine, and Structural Reassignment of Mukonicine

被引：31

作者：

Schuster, Christian ^{[1
]}

Roennefahrt, Marika ^{[1
]}

Julich-Gruner, Konstanze K. ^{[1
]}

Jaeger, Anne ^{[1
]}

Schmidt, Arndt W. ^{[1
]}

Knoelker, Hans-Joachim ^{[1
]}

机构：

[1] Tech Univ Dresden, Dept Chem, D-01069 Dresden, Germany

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 01期

关键词：

alkaloids; catalysis; cyclization; natural products; palladium; 1ST TOTAL-SYNTHESIS; TRANSITION-METAL-COMPLEXES; PALLADIUM-CATALYZED APPROACH; CARBAZOLE ALKALOIDS; ORGANIC-SYNTHESIS; MURRAYA-KOENIGII; RING-CLOSURE; GIRINIMBINE; MAHANIMBINE; ETHERS;

D O I：

10.1055/s-0035-1560359

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using the palladium(II)-catalyzed oxidative cyclization of a diarylamine and the annulation of a dimethylpyran ring by Lewis acid promoted reaction with prenal as key steps, the total syntheses of the 6-oxygenated pyrano[3,2-a]carbazole alkaloids koenine and koenimbine, and of the 6,7-dioxygenated pyrano[3,2-a]carbazole alkaloids koenigine and koenigicine (koenimbidine, koenidine) were achieved. Moreover, these studies led to an improved synthetic route to the 2,6-dioxygenated carbazole alkaloid glycozolidol. Mukonicine, originally published as 6,8-dimethoxypyrano[3,2-a]carbazole, was found to be identical with koenigicine.

引用

页码：150 / 160

页数：11

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