Radical dearomatization of benzene leading to phenanthridine and phenanthridinone derivatives related to (±)-pancratistatin

被引：28

作者：

Crich, David ^{[1
]}

Krishnamurthy, Venkataramanan ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 29期

基金：

美国国家科学基金会;

关键词：

radical; arylation; cyclohexadienyl; dearomatization; phenanthridinone;

D O I：

10.1016/j.tet.2006.04.096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the phenanthridinone nucleus common to the Amaryllidaceae series of natural products is achieved by a sequence involving tributylstannane-mediated, benzeneselenol-catalyzed addition of ortho-nitrogen functionalized aryl radicals to benzene, yielding aryl-substituted cyclohexadienes. These cyclohexadienes may be manipulated by oxidative ring closure sequences to generate functionalized phenanthridines. Beginning from 2-hydroxy-6-iodopiperonic acid a key intermediate in the Danishefsky synthesis of (+/-)-pancratistatin is achieved in two steps. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：6830 / 6840

页数：11

共 81 条

[1] CONSTRUCTION OF QUATERNARY CARBON CENTERS BY PALLADIUM-CATALYZED INTRAMOLECULAR ALKENE INSERTIONS - TOTAL SYNTHESIS OF THE AMARYLLIDACEAE ALKALOIDS (+/-)-TAZETTINE AND (+/-)-6A-EPIPRETAZETTINE [J].