A Concise Total Synthesis of (+)-Scholarisine A Empowered by a Unique C-H Arylation

被引：112

作者：

Smith, Myles W. ^{[1
]}

Snyder, Scott A. ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 35期

关键词：

HOMOLYTIC AROMATIC-SUBSTITUTION; STEREOSELECTIVE-SYNTHESIS; ACID CATALYSIS; DERIVATIVES; 2-PYRONES; EFFICIENT; CYCLOADDITIONS; HETEROCYCLES; ADDUCTS; IMINES;

D O I：

10.1021/ja406546k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The structurally unique akuammiline alkaloid (+)-scholarisine A was synthesized in 14 steps from a known enone (15 steps from commercial materials) through a route empowered by a unique C-H arylation reaction to forge its polycyclic core. Additional key steps include a pyrone Diels-Alder reaction and a radical cyclization/Keck allylation to fashion the core cage polycycle and one of the molecule's quaternary centers, as well as the use of a carefully positioned pendant hydroxyl group to facilitate the chemoselective reduction of an extremely unreactive lactam in the presence of a readily reduced lactone.

引用

页码：12964 / 12967

页数：4

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