Total Synthesis of (±)-Didehydrostemofoline (asparagamine a) and (±)-lsodidehydrostemofoline

被引：88

作者：

Brüggemann, M ^{[1
]}

McDonald, AI ^{[1
]}

Overman, LE ^{[1
]}

Rosen, MD ^{[1
]}

Schwink, L ^{[1
]}

Scott, JP ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 50期

关键词：

D O I：

10.1021/ja0388820

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total syntheses of (±)-didehydrostemofoline (1) and (±)-isodidehydrostemofoline (3) are reported. The synthesis begins with the Diels?Alder reaction of readily available pyrrole 9 and ethyl (E)-3-nitroacrylate, the latter serving as a regioinverted equivalent of ketene. After hydrogenation to prevent retro-Diels?Alder reaction, the major cycloadduct is transformed to 7-azabicyclo[2.2.1]heptanol 14. Aza-Cope?Mannich reaction of the formaldiminium derivative of 14 delivers 1-azatricyclo[5.3.0.04.10]decane 15, which in 15 additional steps is converted to 1 and 3. Copyright © 2003 American Chemical Society.

引用

页码：15284 / 15285

页数：2

共 21 条

[1] A DIRECT SYNTHESIS OF OLEFINS BY REACTION OF CARBONYL-COMPOUNDS WITH LITHIO DERIVATIVES OF 2-[ALKYL-SULFONYL OR (2'-ALKENYL)-SULFONYL OR BENZYL-SULFONYL]-BENZOTHIAZOLES [J].