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
[71]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[72]   The first total synthesis of nakadomarin A [J].
Nagata, T ;
Nakagawa, M ;
Nishida, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (25) :7484-7485
[73]  
Nagata T, 1996, CHEM PHARM BULL, V44, P451
[74]   New approaches to total synthesis of manzamine A, ircinal A and related compounds [J].
Nakagawa, M ;
Torisawa, Y ;
Uchida, H ;
Nishida, A .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1999, 57 (11) :1004-1015
[75]   DIHYDROPYRIDINONE APPROACH TO MANZAMINES - AN EXPEDIENT CONSTRUCTION OF THE TETRACYCLIC CORE OF MANZAMINE-A [J].
NAKAGAWA, M ;
TORISAWA, Y ;
HOSAKA, T ;
TANABE, K ;
DATE, T ;
OKAMURA, K ;
HINO, T .
TETRAHEDRON LETTERS, 1993, 34 (28) :4543-4546
[76]  
Nishida A, 1998, SYNLETT, P389
[77]   Enantioselective Diels-Alder reactions catalyzed by chiral 1,1′-(2,2′-bisacylamino)binaphthalene-ytterbium complex [J].
Nishida, A ;
Yamanaka, M ;
Nakagawa, M .
TETRAHEDRON LETTERS, 1999, 40 (08) :1555-1558
[78]  
NOWAK W, 1993, LIEBIGS ANN CHEM, P153
[79]   Asymmetric total synthesis of (-)-nakadomarin A [J].
Ono, K ;
Nakagawa, M ;
Nishida, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (15) :2020-2023
[80]  
Pandit UK, 1999, EUR J ORG CHEM, V1999, P959