Total Synthesis of 7-and 8-Oxygenated Pyrano[3,2-a]carbazole and Pyrano[2,3-a]carbazole Alkaloids via Boronic Acid-Catalyzed Annulation of the Pyran Ring

被引：55

作者：

Julich-Gruner, Konstanze K. ^{[1
]}

Kataeva, Olga ^{[1
]}

Schmidt, Arndt W. ^{[1
]}

Knoelker, Hans-Joachim ^{[1
]}

机构：

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 28期

关键词：

alkaloids; C-H bond activation; natural products; palladium; stereoselective catalysis; ACTIVE CARBAZOLE ALKALOIDS; CLAUSENA EXCAVATA. ISOLATION; TRANSITION-METAL-COMPLEXES; MURRAYA-KOENIGII; STRUCTURAL ELUCIDATION; ORGANIC-SYNTHESIS; MAHANINE; CONSTITUENTS; APOPTOSIS; CLOSURE;

D O I：

10.1002/chem.201403143

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The boronic acid-catalyzed annulation of citral opens up a short route to oxygenated cyclized monoterpenoid pyranocarbazole alkaloids. Thus, murrayamine-D is available in only three steps and 55% overall yield from the corresponding carbazole precursor.

引用

页码：8536 / 8540

页数：5

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