Tandem radical reactions of isonitriles with 2-pyridonyl and other aryl radicals: Scope and limitations, and a first generation synthesis of (+/-)-camptothecin

被引：101
作者：
Curran, DP
Liu, H
Josien, H
Ko, SB
机构：
[1] Department of Chemistry, University of Pittsburgh, Pittsburgh
来源：
TETRAHEDRON | 1996年 / 52卷 / 35期
关键词：
D O I：
10.1016/0040-4020(96)00633-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Photolysis of N-propargyl-6-halo-2-pyridones and related aromatic halides in the presence of aryl isonitriles provides tetra- and pentacyclic products in a single step by a sequence of radical addition to the isonitrile followed by two cyclizations. The scope and limitations of the process are described along with a first generation synthesis of racemic camptothecin. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：11385 / 11404
页数：20
相关论文
共 68 条
[1]   THE INVENTION OF RADICAL REACTIONS .33. HOMOLOGATION REACTIONS OF CARBOXYLIC-ACIDS BY RADICAL-CHAIN CHEMISTRY [J].
BARTON, DHR ;
CHERN, CY ;
JASZBERENYI, JC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (02) :407-425
[2]   THE INVENTION OF CHEMICAL-REACTIONS OF RELEVANCE TO THE CHEMISTRY OF NATURAL-PRODUCTS [J].
BARTON, DHR .
PURE AND APPLIED CHEMISTRY, 1994, 66 (10-11) :1943-1954
[3]   IRON(III) MEDIATED TRANSFORMATIONS OF CYCLOPROPYLTRIMETHYLSILYL ETHERS .1. FREE-RADICAL TANDEM RING EXPANSION-CYCLIZATION REACTIONS FOR THE RAPID CONSTRUCTION OF [N30] BICYCLIC RING-SYSTEMS [J].
BOOKERMILBURN, KI ;
THOMPSON, DF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (18) :2315-2321
[4]   OXIDATION DURING REDUCTIVE CYCLIZATIONS USING BU3SNH [J].
BOWMAN, WR ;
HEANEY, H ;
JORDAN, BM .
TETRAHEDRON, 1991, 47 (48) :10119-10128
[5]  
BOWMAN WR, 1995, TETRAHEDRON LETT, V36, P5623
[6]   RECENT ADVANCES IN THE USE OF TANDEM REACTIONS FOR ORGANIC-SYNTHESIS [J].
BUNCE, RA .
TETRAHEDRON, 1995, 51 (48) :13103-13159
[7]   VITAMIN-B-12-CATALYZED C,C-BOND FORMATION - SYNTHESIS OF JASMONATES VIA SEQUENTIAL RADICAL REACTION [J].
BUSATO, S ;
SCHEFFOLD, R .
HELVETICA CHIMICA ACTA, 1994, 77 (01) :92-99
[8]   A 6-STEP SYNTHESIS OF (+/-)-CAMPTOTHECIN [J].
COMINS, DL ;
HONG, H ;
SAHA, JK ;
GAO, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5120-5121
[9]   A 10-STEP, ASYMMETRIC-SYNTHESIS OF (S)-CAMPTOTHECIN [J].
COMINS, DL ;
BAEVSKY, MF ;
HONG, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10971-10972
[10]   ASYMMETRIC-SYNTHESIS OF CAMPTOTHECIN ALKALOIDS - A 9-STEP SYNTHESIS OF (S)-CAMPTOTHECIN [J].
COMINS, DL ;
HONG, H ;
JIANHUA, G .
TETRAHEDRON LETTERS, 1994, 35 (30) :5331-5334
1234567