Efficient synthesis of the azaspirocyclic core structure of halichlorine and pinnaic acid by intramolecular acylnitroso ene reaction

被引:44
作者
Matsumura, Y [1 ]
Aoyagi, S [1 ]
Kibayashi, C [1 ]
机构
[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan
关键词
D O I
10.1021/ol030073y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A new efficient strategy for the construction of the 6-azaspiro[4.5]decane ring system was developed using intramolecular ene reaction of the acylnitroso compound. The spirocyclic ene product obtained as a single diastereomer was subsequently subjected to highly stereoselective ethynylation, leading to the azaspirodecane core of halichlorine and the pinnaic acids.
引用
收藏
页码:3249 / 3252
页数:4
相关论文
共 41 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]  
BOGER DL, 1987, HETEREO DIELSALDER M
[4]  
Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4450, DOI 10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO
[5]  
2-M
[6]  
Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4453, DOI 10.1002/1521-3773(20011203)40:23<4453::AID-ANIE4453>3.0.CO
[7]  
2-4
[8]   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
[9]   C-NITROSOFORMAMIDES, A NEW CLASS OF TRANSIENT DIENOPHILES FORMED BY OXIDATION OF N-HYDROXYUREAS [J].
CHRISTIE, CC ;
KIRBY, GW ;
MCGUIGAN, H ;
MACKINNON, JWM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2469-2473
[10]   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