Gold-Catalyzed One-Step Construction of 2,3-Dihydro-1H-Pyrrolizines with an Electron-Withdrawing group in the 5-position: A Formal Synthesis of 7-Methoxymitosene

被引：136
作者：
Yan, Ze-Yi [1 ]
Xiao, Yuanjing [1 ]
Zhang, Liming [1 ]
机构：
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 34期
基金：
美国国家科学基金会;
关键词：
carbene; gold; homogeneous catalysis; mitosene; nitrene; CYCLOISOMERIZATION; DERIVATIVES; PYRROLE; COMPLEXES; EFFICIENT; PLATINUM; ACCESS;
D O I：
10.1002/anie.201203678
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
What a ring formation! Bicyclic dihydropyrrolizines with an electron-withdrawing group (EWG) at the 5-position are formed in one step from linear azidoenynes under gold catalysis. This novel route involves the use of azide as a nitrene precursor, electronically-controlled regioselectivity, and the generation of destabilized 1-azapentadienium ions and their pericyclic reactions. This method was used for a formal synthesis of 7-methoxymitosene (see scheme).
引用
收藏
页码：8624 / 8627
页数：4
相关论文
共 57 条
[1]   Novel substituted and fused pyrrolizine derivatives: Synthesis, anti-inflammatory and ulcerogenecity studies [J].
Abbas, Safinaz E. ;
Awadallah, Fadi M. ;
Ibrahim, Nashwa A. ;
Gouda, Ahmed M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :482-491
[2]  
Alickmann D, 2002, EUR J ORG CHEM, V2002, P1523
[3]   MITOMYCIN ANTIBIOTICS . SYNTHETIC STUDIES .5. PREPARATION OF 7-METHOXYMITOSENE [J].
ALLEN, GR ;
POLETTO, JF ;
WEISS, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (09) :2897-&
[4]  
[Anonymous], 2011, ANGEW CHEM
[5]  
[Anonymous], 2007, ANGEW CHEM
[6]   Synthesis of Fused Carbocycles via a Selective 6-Endo Dig Gold(I)-Catalyzed Carbocyclization [J].
Barabe, Francis ;
Levesque, Patrick ;
Korobkov, Ilia ;
Barriault, Louis .
ORGANIC LETTERS, 2011, 13 (20) :5580-5583
[7]  
Bhunia S., 2012, ANGEW CHEM, V124, P2993
[8]   Gold-Catalyzed Oxidative Cyclizations of cis-3-En-1-ynes To Form Cyclopentenone Derivatives [J].
Bhunia, Sabyasachi ;
Ghorpade, Satish ;
Huple, Deepak B. ;
Liu, Rai-Shung .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (12) :2939-2942
[9]  
Boers RB, 2002, EUR J ORG CHEM, V2002, P189, DOI 10.1002/1099-0690(20021)2002:1<189::AID-EJOC189>3.0.CO
[10]  
2-8
123456