Amidopalladation of alkoxyallenes applied in the synthesis of an enantiopure 1-ethylquinolizidine frog alkaloid

被引：65

作者：

Kinderman, SS

de Gelder, R

van Maarseveen, JH

Schoemaker, HE

Hiemstra, H

Rutjes, FPJT

机构：

[1] Catholic Univ Nijmegen, NSRIM, Dept Organ & Inorgan Chem, NL-6525 ED Nijmegen, Netherlands

[2] Univ Amsterdam, Inst Mol Chem, NL-1018 WS Amsterdam, Netherlands

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 13期

关键词：

D O I：

10.1021/ja039919j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium-catalyzed amidation of alkoxyallenes has been developed for the construction of linear allylic N,O-acetals under basic conditions involving (cyclic) amides, sulfonamides, carbamates, and amidophosphates. Application of the methodology provided access to the enantiopure 1-ethylquinolizidine structural motif, which is a key synthon in the synthesis of the naturally occurring poisonous frog quinolizidine 233A and derivatives such as the 1-epi-isomer of quinolizidine 207I. Copyright © 2004 American Chemical Society.

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页码：4100 / 4101

页数：2

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