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
收藏
页码：879 / 882
页数：4
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