Total Synthesis of Leuconoxine, Melodinine E, and Mersicarpine through Radical Translocation-Cyclization Cascade

被引：28
|
作者：
Kim, Ryan [1 ]
Ferreira, Andrew J. [1 ]
Beaudry, Christopher M. [1 ]
机构：
[1] Oregon State Univ, Dept Chem, 153 Gilbert Hall, Corvallis, OR 97333 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 36期
关键词：
leuconoxine; melodinine E; mersicarpine; radical reactions; total synthesis; OXIDATIVE CLEAVAGE; FORMAL SYNTHESIS; REACTIVITY; ALKALOIDS; BONDS; (-)-LEUCONOXINE; LEUCONODINES;
D O I：
10.1002/anie.201907455
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The Aspidosperma alkaloids leuconoxine, melodinine E, and mersicarpine were synthesized. The approach features a key cascade radical reaction. A 1,5-hydrogen atom transfer is followed by spontaneous 5-exo-trig cyclization to construct the central indoline architecture. Late-stage differentiation of the radical cyclization product by chemoselective oxidation allows production of either the leuconoxine/melodinine E or mersicarpine structure.
引用
收藏
页码：12595 / 12598
页数：4
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