Domino coupling relay approach to polycyclic pyrrole-2-carboxylates

被引:209
作者
Yamamoto, Y [1 ]
Hayashi, H [1 ]
Saigoku, T [1 ]
Nishiyama, H [1 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan
关键词
D O I
10.1021/ja053408a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
CuBr2-catalyzed three-component coupling of N-benzylallylamine, ethyl glyoxalate, and terminal alkynes afforded glycine-tethered 1,6-enynes, which were further transformed into polycyclic pyrrole-2-carboxylates via novel cycloisomerization/Diels-Alder cycloaddition/dehydrogenation sequence under iridium-catalyzed conditions. Copyright © 2005 American Chemical Society.
引用
收藏
页码:10804 / 10805
页数:2
相关论文
共 34 条
[1]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[2]   Pyrrole syntheses by multicomponent coupling reactions [J].
Balme, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6238-6241
[3]   Group 6 Fischer carbene complexes:: "chemical multitalents" for multi-component reactions [J].
Barluenga, J ;
Fernández-Rodríguez, MA ;
Aguilar, E .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (03) :539-587
[4]   Design, synthesis, conformational analysis and application of azabicycloalkane amino acids as constrained dipeptide mimics [J].
Belvisi, L ;
Colombo, L ;
Manzoni, L ;
Potenza, D ;
Scolastico, C .
SYNLETT, 2004, (09) :1449-1471
[5]   Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels-Alder reactions [J].
Boger, DL ;
Boyce, CW ;
Labroli, MA ;
Sehon, CA ;
Jin, Q .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :54-62
[6]   Development of 5-(aminomethyl)pyrrole-2-carboxylic acid as a constrained surrogate of Gly-ΔAla and its application in peptidomimetic studies [J].
Chakraborty, TK ;
Mohan, BK ;
Kumar, SK ;
Kunwar, AC .
TETRAHEDRON LETTERS, 2002, 43 (14) :2589-2592
[7]   Iridium(I)-catalyzed cycloisomerization of enynes [J].
Chatani, N ;
Inoue, H ;
Morimoto, T ;
Muto, T ;
Murai, S .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4433-4436
[8]   Organometallic alkane CH activation [J].
Crabtree, RH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :4083-4091
[9]   Palladium-catalyzed multicomponent coupling of alkynes, imines, and acid chlorides: A direct and modular approach to pyrrole synthesis [J].
Dhawan, R ;
Arndtsen, BA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :468-469
[10]   Unnatural amino acids as probes of protein structure and function [J].
Dougherty, DA .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2000, 4 (06) :645-652