A Photoinduced Cyclization Cascade-Total Synthesis of (-)-Leuconoxine

被引：26
作者：
Pfaffenbach, Magnus [1 ]
Gaich, Tanja [1 ]
机构：
[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 17期
关键词：
fenestrane; indole alkaloid; total synthesis; transannular cylization; witkop photocyclization; ENANTIOSELECTIVE TOTAL SYNTHESES; MONOTERPENOID INDOLE ALKALOIDS; LEUCONOTIS-GRIFFITHII; PENICILLIUM-GRISEOFULVUM; DACRYDIUM-CUPRESSINUM; 2-SUBSTITUTED INDOLES; FUNGICOLOUS ISOLATE; FORMAL SYNTHESIS; PENIFULVINS-B; ESSENTIAL OIL;
D O I：
10.1002/chem.201500656
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A protecting-group-free and enantioselective total synthesis of the monoterpenoid indole alkaloid (-)-leuconoxine was accomplished. The key step comprises a novel photoinduced domino macrocyclization/transannular cyclization involving the Witkop cyclization, for which additional mechanistic evidence is provided. This process furnishes a diaza[5.5.6.6]fenestrane skeleton, which is a hitherto unprecedented structure element.
引用
收藏
页码：6355 / 6357
页数：3
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