An approach to the skeleton of the Securinega alkaloids.: The total synthesis of (±)-securinine

被引:69
作者
Liras, S [1 ]
Davoren, JE [1 ]
Bordner, J [1 ]
机构
[1] Pfizer Global Res & Dev, Groton, CT 06340 USA
关键词
D O I
10.1021/ol0070482
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The concise total synthesis of securinine in nine steps from readily available starting materials is described. Key steps of the synthesis include an addition of a silyloxyfuran to an in situ generated iminium ion and a novel ring closing metathesis reaction.
引用
收藏
页码:703 / 706
页数:4
相关论文
共 25 条
[1]   SECURININE ALKALOIDS - A NEW CLASS OF GABA RECEPTOR ANTAGONIST [J].
BEUTLER, JA ;
KARBON, EW ;
BRUBAKER, AN ;
MALIK, R ;
CURTIS, DR ;
ENNA, SJ .
BRAIN RESEARCH, 1985, 330 (01) :135-140
[2]   Vinylogous Mannich reactions: Some theoretical studies on the origins of diastereoselectivity [J].
Bur, SK ;
Martin, SF .
ORGANIC LETTERS, 2000, 2 (22) :3445-3447
[3]   The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].
Casiraghi, G ;
Zanardi, F ;
Appendino, G ;
Rassu, G .
CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972
[4]  
COTE R, 1989, HETEROCYCLES, V28, P987
[5]   RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].
GRUBBS, RH ;
MILLER, SJ ;
FU, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452
[6]   A novel intramolecular Diels-Alder approach to securinega alkaloids: formal synthesis of securinine [J].
Honda, T ;
Namiki, H ;
Kudoh, M ;
Watanabe, N ;
Nagase, H ;
Mizutani, H .
TETRAHEDRON LETTERS, 2000, 41 (31) :5927-5930
[7]   TOTAL SYNTHESIS OF SECURININE AND VIROSECURININE [J].
HORII, Z ;
HANAOKA, M ;
YAMAWAKI, Y ;
TAMURA, Y ;
SAITO, S ;
SHIGEMATSU, N ;
KOTERA, K ;
YOSHIKAWA, H ;
SATO, Y ;
NAKAI, H ;
SUGIMOTO, N .
TETRAHEDRON, 1967, 23 (03) :1165-+
[8]   ASYMMETRIC INDUCTION IN THE ADDITION-REACTIONS OF CHIRAL SULFINYLALLYL ANIONS (AMBIDENT NUCLEOPHILES) WITH ENONES (AMBIDENT ELECTROPHILES) - RING-CLOSURE OF ENOL THIOETHER KETONES [J].
HUA, DH ;
VENKATARAMAN, S ;
COULTER, MJ ;
SINAIZINGDE, G .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :719-728
[9]  
IMADO S, 1965, CHEM PHARM BULL, V13, P643
[10]  
Maier ME, 2000, ANGEW CHEM INT EDIT, V39, P2073, DOI 10.1002/1521-3773(20000616)39:12<2073::AID-ANIE2073>3.0.CO