Synthesis of the tricyclic triamine core of martinelline and martinellic acid

被引：87

作者：

Snider, BB ^{[1
]}

Ahn, Y ^{[1
]}

Foxman, BM ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 17期

基金：

美国国家卫生研究院;

关键词：

alkaloids; cycloadditions; azides; cyclopropanes;

D O I：

10.1016/S0040-4039(99)00461-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tricyclic triamine core 27 of martinellic acid (2) has been prepared stereospecifically in eight steps from 2-hydroxymethylaniline in 11% overall yield. The key steps are the addition of 2-hydroxymethylaniline to vinylcyclopropane 14 to prepare cycloaddition precursor 19 in only two steps and an intramolecular [3+2] azomethine ylide cycloaddition reaction to produce tetracycle 20 with >9:1 diastereoselectivity. (C) 1999 Elsevier Science Ltd, All rights reserved.

引用

页码：3339 / 3342

页数：4

共 13 条

[1]

[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3

[2]

AUBE J, 1998, 216 NAT M AM CHEM SO

[3] THE STABILIZED IMINIUM YLIDE OLEFIN [3 + 2] CYCLOADDITION REACTION - TOTAL SYNTHESIS OF SCELETIUM ALKALOID-A4 [J].