A novel total synthesis of antibiotic carbazole alkaloid carbazomycin G

被引：69

作者：

Hagiwara, H ^{[1
]}

Choshi, T ^{[1
]}

Fujimoto, H ^{[1
]}

Sugino, E ^{[1
]}

Hibino, S ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2000年 / 56卷 / 32期

关键词：

allenes; electrocyclic reactions; polycyclic heterocyclic compounds; quinonoid compounds;

D O I：

10.1016/S0040-4020(00)00543-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of carbazomycin G (1) has been newly completed in seven steps. The 1,3-dioxygenated carbazole (4) via the 3-methoxy-1-methoxymethyloxycarbazole (11) as a synthetic precursor was synthesized by using the allene-mediated electrocyclic reaction of a 6 pi electron system generating from the 2-propargylindole derivative (10), which was derived from the 3-vinylindole (8) in three steps. Finally, the oxidation of the phenol (4) followed by the addition of methyl lithium to the carbazole-1,4-quinone (3) provided carbazomycin G (1). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5807 / 5811

页数：5

共 39 条

[1] THE OXYGEN-CARRYING SYNTHETIC CHELATE COMPOUNDS .7. PREPARATION [J].