Convergency and divergency as strategic elements in total synthesis:: The total synthesis of (-)-drupacine and the formal total synthesis of (±)-Cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine

被引：59

作者：

Liu, Qi ^{[1
]}

Ferreira, Eric M. ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Arnold & Beckman Labs Chem Synth, Pasadena, CA 91125 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 19期

关键词：

D O I：

10.1021/jo0710883

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A concise route toward the syntheses of (-)-drupacine and (+)- and (-)-cephalotaxine has been developed. The syntheses rely on Pd(II)-catalyzed aerobic oxidative heterocyclization chemistry, which was employed to rapidly construct an important spirocyclic amine intermediate. A dynamic beta-elimination/conjugate addition process was strategically applied to complete the first asymmetric total synthesis of (-)-drupacine.

引用

页码：7352 / 7358

页数：7

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