Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids

被引：15

作者：

Bautista, Rafael ^{[1
]}

Jerezano, Alberto V. ^{[1
]}

Tamariz, Joaquin ^{[1
]}

机构：

[1] Inst Politecn Nacl, Escuela Nacl Ciencias Biol, Dept Quim Organ, Mexico City 11340, DF, Mexico

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 21期

关键词：

1-methoxycarbazoles; alpha-ketoenamines; palladium(II); cyclization; glycozolicine; 1ST TOTAL-SYNTHESIS; MEDIATED TOTAL-SYNTHESIS; TRANSITION-METAL-COMPLEXES; VILSMEIER-HAACK REACTION; DOUBLE N-ARYLATION; ORGANIC-SYNTHESIS; ANTIMICROBIAL ACTIVITY; PROMOTED SYNTHESIS; MURRAYAQUINONE-A; MURRAYAFOLINE-A;

D O I：

10.1055/s-0032-1317175

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.

引用

页码：3327 / 3336

页数：10

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