Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids-first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine

被引：87

作者：

Gruner, Konstanze K. ^{[1
]}

Hopfmann, Thomas ^{[1
]}

Matsumoto, Kazuhiro ^{[2
,3
]}

Jaeger, Anne ^{[1
]}

Katsuki, Tsutomu ^{[2
,3
]}

Knoelker, Hans-Joachim ^{[1
]}

机构：

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

[2] Kyushu Univ, Grad Sch, Fac Sci, Dept Chem,Higashi Ku, Fukuoka 8128581, Japan

[3] Kyushu Univ, Inst Adv Study, Higashi Ku, Fukuoka 8128581, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 07期

基金：

日本学术振兴会;

关键词：

TRANSITION-METAL-COMPLEXES; AQUEOUS HYDROGEN-PEROXIDE; CARBAZOLE ALKALOIDS; ORGANIC-SYNTHESIS; CHEMICAL TAXONOMY; EPOXIDATION; CONSTITUENTS; GIRINIMBINE; MURRAYACINE; OLEFINS;

D O I：

10.1039/c0ob01088j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

oxidative cyclisation provides an efficient approach to pyrano[3,2-a]carbazole alkaloids. Thus, improved routes to girinimbine and murrayacine as well as the first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine are reported. Asymmetric epoxidation of girinimbine led to (-)-trans-dihydroxygirinimbine and the assignment of its absolute configuration.

引用

页码：2057 / 2061

页数：5

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