STEREOCHEMISTRY OF THE ROBINSON-SCHOPF REACTION - STEREOSPECIFIC TOTAL SYNTHESIS OF THE LADYBUG DEFENSE ALKALOIDS PRECOCCINELLINE AND COCCINELLINE

被引：140

作者：

STEVENS, RV

LEE, AWM

机构：

[1] Contribution from the Department of Chemistry, University of California, 90024, Los Angeles, California

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 23期

关键词：

D O I：

10.1021/ja00517a042

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereospecific total synthesis of the ladybug defensive alkaloids coccinelline (1) and precoccinelline (2) is presented. A key step in this synthesis involves a Robinson-Schöpf type of condensation between amine dialdehyde equivalent 32 and acetone dicarboxylic ester to afford 37. A rationale for this stereochemical course is presented. © 1979, American Chemical Society. All rights reserved.

引用

页码：7032 / 7035

页数：4

共 20 条

[1] TOTAL SYNTHESIS OF COCCINELLINE AND PRECOCCINELLINE [J].