Synthesis of a spirocyclic amine related to the marine natural products halichlorine and pinnaic acid

被引:18
作者
Clive, DLJ [1 ]
Wang, H [1 ]
Yu, ML [1 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
halichlorine pinnaic acid; ring closing metathesis; spiro compound; Wittig homologation;
D O I
10.1016/j.tetlet.2005.02.133
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The bis-ester 5 was elaborated into tricyclic lactam 8, which has previously been converted into the spirotricyclic amine 9, a compound that represents a large portion of the marine natural product halichlorine. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码:2853 / 2855
页数:3
相关论文
共 22 条
[11]  
Goldspink NJ, 1999, SYNLETT, P1292
[12]  
Hayakawa I, 2003, HETEROCYCLES, V59, P441
[13]  
HAYAKAWA I, 2004, J CHEM SOC CHEM COMM, P122
[14]   A chiral base desymmetrisation-ring- closing metathesis route to chiral azaspirocycles: Synthesis of core structures related to pinnaic acid and halichlorine [J].
Huxford, T ;
Simpkins, NS .
SYNLETT, 2004, (13) :2295-2298
[15]  
KECK G, 2003, 226 ACS NAT M NEW YO
[16]   Are there concentration effects in enantioselective deprotonation of cyclic ketones? [J].
Majewski, M ;
Wang, F .
TETRAHEDRON, 2002, 58 (23) :4567-4571
[17]   A formal total synthesis of (±)-halichlorine and (±)-pinnaic acid [J].
Matsumura, Y ;
Aoyagi, S ;
Kibayashi, C .
ORGANIC LETTERS, 2004, 6 (06) :965-968
[18]   PROSTAGLANDIN SYNTHESIS .16. THE 3-COMPONENT COUPLING SYNTHESIS OF PROSTAGLANDINS [J].
SUZUKI, M ;
YANAGISAWA, A ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4718-4726
[19]  
Trauner D, 1999, ANGEW CHEM INT EDIT, V38, P3542, DOI 10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO
[20]  
2-I