Synthesis of the tricyclic core of halichlorine

被引:19
作者
Hayakawa, I
Arimoto, H [1 ]
Uemura, D
机构
[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Inst Adv Res, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[3] JST, PRESTO, Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
D O I
10.1039/b402130d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of the tricyclic core of halichlorine, a VCAM-1 expression suppressor, was achieved using ene-yne metathesis cyclization as a key step.
引用
收藏
页码:1222 / 1223
页数:2
相关论文
共 36 条
[1]   Absolute stereochemistry of halichlorine; A potent inhibitor of VCAM-1 induction [J].
Arimoto, H ;
Hayakawa, I ;
Kuramoto, M ;
Uemura, D .
TETRAHEDRON LETTERS, 1998, 39 (08) :861-862
[2]   Synthesis of pinnaic acid; Asymmetric construction of spirocyclic core [J].
Arimoto, H ;
Asano, S ;
Uemura, D .
TETRAHEDRON LETTERS, 1999, 40 (18) :3583-3586
[3]  
Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4450, DOI 10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO
[4]  
2-M
[5]  
Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4453, DOI 10.1002/1521-3773(20011203)40:23<4453::AID-ANIE4453>3.0.CO
[6]  
2-4
[7]   Pinnaic acid and tauropinnaic acid: Two novel fatty acids composing a 6-Azaspiro[4.5]decane unit from the Okinawan bivalve Pinna muricata [J].
Chou, T ;
Kuramoto, M ;
Otani, Y ;
Shikano, M ;
Yazawa, K ;
Uemura, D .
TETRAHEDRON LETTERS, 1996, 37 (22) :3871-3874
[8]   A new route to 2-spiropiperidines [J].
Ciblat, S ;
Canet, JL ;
Troin, Y .
TETRAHEDRON LETTERS, 2001, 42 (29) :4815-4817
[9]   Synthesis of a 6-azaspiro[4.5]decane related to halichlorine and the pinnaic acids [J].
Clive, DLJ ;
Yeh, VSC .
TETRAHEDRON LETTERS, 1999, 40 (49) :8503-8507
[10]   Construction of azaspirocyclic ketones through α-hydroxyiminium ion or α-siloxy epoxide semipinacol rearrangements [J].
Fenster, MDB ;
Patrick, BO ;
Dake, GR .
ORGANIC LETTERS, 2001, 3 (13) :2109-2112