On the structure of Palau'amine: Evidence for the revised relative configuration from chemical synthesis

被引：57

作者：

Lanman, Brian A. ^{[1
]}

Overman, Larry E. ^{[1
]}

Paulini, Ralph ^{[1
]}

White, Nicole S. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 42期

关键词：

D O I：

10.1021/ja074939x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hexacyclic congeners 3 and 4 of palau'amine, which incorporate both guanidine functional groups and have the cis configuration of the azabicyclo[3-3.0]octane core, are prepared in 14 steps from cycloadduct 6. Synthetic access to these analogues allows the first direct comparison of NMR data for hexacyclic diguanidine structures having the originally proposed cis-azabicyclo[3.3. 01]octan e fragment with data for natural alkaloids of the palau'amine family. This comparison provides convincing evidence in favor of the recently proposed structural revision of these marine alkaloids, fully supporting the trans configuration of the central azabicyclo[3.3.0]octane ring system of palau'amine and congeners.

引用

页码：12896 / 12900

页数：5

共 24 条

[21] A new entry for the synthesis of N-acyl-N′-substituted guanidines [J].