SYNTHETIC STUDIES ON QUINOCARCIN - TOTAL SYNTHESIS OF (+/-)-QUINOCARCINAMIDE VIA DIPOLE CYCLOADDITION OF AN AZOMETHINE YLIDE GENERATED BY NBS OXIDATION

被引：51

作者：

FLANAGAN, ME ^{[1
]}

WILLIAMS, RM ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 21期

关键词：

D O I：

10.1021/jo00126a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The total synthesis of (+/-)-quinocarcinamide and a formal total synthesis of the antitumor, antibiotic quinocarcin involving a [3 + 2] dipolar cycloaddition reaction is described. The synthesis involves as a key step an NBS oxidation of an allylic tertiary amine to an imminium ion which is converted in situ into an azomethine ylide. Aspects of the ylide formation and a rationale for the regio- and stereocontrol for the cycloaddition process are discussed.

引用

页码：6791 / 6797

页数：7

共 52 条

[1]

A SYNTHESIS OF (+/-)-7-METHOXYCARBONYL-2-(3-METHOXYPHENYLMETHYLIDENE)-8-METHYL-3,8-DIAZABICYCLO[3.2.1]OCTAN-4-ONE (1B) USING DIPOLAR CYCLOADDITION TO A 3-OXIDOPYRAZINIUM [J].