Novel syntheses of murrayaquinone A and furostifoline through 4-oxygenated carbazoles by allene-mediated electrocyclic reactions starting from 2-chloroindole-3-carbaldehyde

被引：54

作者：

Hagiwara, H ^{[1
]}

Choshi, T ^{[1
]}

Nobuhiro, J ^{[1
]}

Fujimoto, H ^{[1
]}

Hibino, S ^{[1
]}

机构：

[1] Fukuyama Univ, Fac Pharm & Pharmaceut Sci, Grad Sch Pharm & Pharmaceut Sci, Fukuyama, Hiroshima 7290292, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2001年 / 49卷 / 07期

关键词：

murrayaquinone A; carbazole-1,4-quinone; furostifoline; furo[3,2-alpha]carbazole; allene; electrocyclic reaction;

D O I：

10.1248/cpb.49.881

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The formal total synthesis of murrayaquinone A (1) and the total synthesis of furostifoline (5) were completed by the construction of 4-oxygenated 3-methylcarbazoles 7 based on a new type of electrocyclic reaction through 2-alkenyl-3-allenylindole intermediates 8 derived from the 2-alkenyl-3-propargylindoles 9, starting from 2-chloroindole-3-carbaldehyde (11). The N,O-bisbenzyloxymethyl group of 16c and 22 underwent a Birch reduction followed by treatment with Triton B to produce the known 4-hydroxy-3-methylcarbazole (7a) and 4-hydroxy-3-methylfuro[3,2-a]carbazole (7b) as precursors of murrayaquinone A (1) and furostifoline (5), respectively, The trifluoromethanesulfonyloxy-3-methylfuro[3,2-a]carbazole (24), prepared from 7b, was subjected to reductive cleavage to provide furostifoline (5).

引用

页码：881 / 886

页数：6