Total Synthesis of the Akuammiline Alkaloid Picrinine

被引：87

作者：

Smith, Joel M. ^{[1
]}

Moreno, Jesus ^{[1
]}

Boal, Ben W. ^{[1
]}

Garg, Neil K. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 12期

基金：

美国国家科学基金会;

关键词：

SCHOLARIS R BR; ALSTONIA-SCHOLARIS; (+/-)-ASPIDOPHYLLINE; (+)-SCHOLARISINE; STRICTAMINE; CONVERSION; OXIDATION; KETONES; SYSTEM; LEAVES;

D O I：

10.1021/ja501780w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product's carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine.

引用

页码：4504 / 4507

页数：4

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