Total Synthesis of Indole Alkaloid Alsmaphorazine D

被引：34

作者：

Zhu, Chenlong ^{[1
]}

Liu, Zhaobo ^{[1
]}

Chen, Guanyu ^{[1
]}

Zhang, Kai ^{[1
]}

Ding, Hanfeng ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 03期

关键词：

cyclization; epimerization; oxidative coupling; pyrroloindoles; total synthesis; ENANTIOSPECIFIC TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; MACROCYCLIZATION-TRANSANNULAR CYCLIZATION; CERIUM(IV) AMMONIUM-NITRATE; GENERAL-APPROACH; ALSTONIA-SCHOLARIS; STEREOCHEMICAL CONTROL; RADICAL CYCLIZATIONS; BREVIANAMIDE E; IN-VITRO;

D O I：

10.1002/anie.201409827

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise total synthesis of rac-alsmaphorazine D has been described for the first time. The efficient synthetic strategy features four key transformations: 1) a catalytic intramolecular oxidative cyclization for the delta-lactamindole backbone; 2) an oxidative cyclic aminal formation for the hexahydropyrrolo[2,3-b]pyrrole framework; 3) a transannular radical cyclization for the construction of the diazabicyclo-[3.3.1]nonane structure; and 4) a one-pot desilylation/double epimerization reaction that affirms the relative stereochemistry.

引用

页码：879 / 882

页数：4

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