Preparation of nitrogen-containing heterocycles using ring-closing metathesis (RCM) and its application to natural product synthesis

被引:64
作者
Arisawa, Mitsuhiro
Nishida, Atsushi
Nakagawa, Masako
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
[2] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
[3] Kanagawa Univ, Dept Chem, Fac Sci, Hiratsuka, Kanagawa 2591293, Japan
关键词
nitrogen-containing heterocycles; ring-closing metathesis (RCM); chiral bicyclic lactams; azacycloundecenes; axially chiral macrolactams; 1,2-dihydroquinolines; 2-quinolinones; indoles; silyl-enol ether ene metathesis; isomerization of terminal olefins; natural product synthesis;
D O I
10.1016/j.jorganchem.2006.08.009
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Our synthetic study of nitrogen-containing heterocycles using ring-closing metathesis (RCM), such as chiral bicyclic lactams, azacycloundecenes, axially chiral macrolactams, 1,2-dihydroquinolines, 2-quinolinones and indoles, including a development of silyl-enol ether ene metathesis and isomerization of terminal olefins, are described. Their applications to natural product synthesis are also reported. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:5109 / 5121
页数:13
相关论文
共 111 条
[41]   Macrocycles by ring-closing metathesis [J].
Furstner, A ;
Langemann, K .
SYNTHESIS-STUTTGART, 1997, (07) :792-&
[42]  
Fürstner A, 1998, ANGEW CHEM INT EDIT, V37, P1734, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1734::AID-ANIE1734>3.0.CO
[43]  
2-6
[44]   Exploiting the reversibility of olefin metathesis.: Syntheses of macrocyclic trisubstituted alkenes and (R,R)-(-)-pyrenophorin [J].
Fürstner, A ;
Thiel, OR ;
Ackermann, L .
ORGANIC LETTERS, 2001, 3 (03) :449-451
[45]   PEPTIDOMIMETICS FOR RECEPTOR LIGANDS DISCOVERY, DEVELOPMENT, AND MEDICAL PERSPECTIVES [J].
GIANNIS, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (09) :1244-1267
[46]   Synthesis of macrocyclic lactams and lactones via ring-closing olefin metathesis [J].
Goldring, WPD ;
Hodder, AS ;
Weiler, L .
TETRAHEDRON LETTERS, 1998, 39 (28) :4955-4958
[47]  
Grethe G., 1983, CHEM HETEROCYCLIC 4, V23, P279
[48]   Recent developments in indole ring synthesis-methodology and applications [J].
Gribble, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075
[49]  
Grossmith CE, 1999, SYNLETT, P1660
[50]   Olefin metathesis [J].
Grubbs, RH .
TETRAHEDRON, 2004, 60 (34) :7117-7140