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
收藏
页码:3327 / 3336
页数:10
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