Synthetic study of zoanthamine alkaloids: The C-ring model possessing three consecutive quaternary carbons

被引:18
作者
Hirai, G
Oguri, H
Hirama, M [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
[2] Japan Sci & Technol Corp, CREST, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1246/cl.1999.141
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Stereo-controlled construction of the C-ring model (4) of zoanthamine alkaloids was achieved via a SmI2-mediated Simmons-Smith reaction.
引用
收藏
页码:141 / 142
页数:2
相关论文
共 21 条
[1]   ORGANOCOPPER CONJUGATE ADDITION-REACTION IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].
ALEXAKIS, A ;
BERLAN, J ;
BESACE, Y .
TETRAHEDRON LETTERS, 1986, 27 (09) :1047-1050
[2]   Epioxyzoanthamine, a new zoanthamine-type alkaloid and the unusual deuterium exchange in this series. [J].
Daranas, AH ;
Fernández, JJ ;
Gavín, JA ;
Norte, M .
TETRAHEDRON, 1998, 54 (27) :7891-7896
[3]  
Fukuzawa S., 1995, HETEROCYCL COMMUN, V1, P207
[4]   Synthetic studies of zoanthamine/norzoanthamine alkaloids: Construction of the heterocyclic aminal core (CDEFG ring) [J].
Hikage, N ;
Furukawa, H ;
Takao, K ;
Kobayashi, S .
TETRAHEDRON LETTERS, 1998, 39 (34) :6241-6244
[5]   Synthetic studies of zoanthamine/norzoanthamine alkaloids: Advanced intermediate for the heterocyclic aminal core [J].
Hikage, N ;
Furukawa, H ;
Takao, K ;
Kobayashi, S .
TETRAHEDRON LETTERS, 1998, 39 (34) :6237-6240
[6]   DIVALENT SAMARIUM-INDUCED CYCLOPROPANATION OF LITHIUM ENOLATES - A ONE-POT SYNTHESIS OF CYCLOPROPANOLS FROM KETONES [J].
IMAMOTO, T ;
TAKIYAMA, N .
TETRAHEDRON LETTERS, 1987, 28 (12) :1307-1308
[7]   Structure-activity relationship of norzoanthamine exhibiting significant inhibition of osteoporosis [J].
Kuramoto, M ;
Hayashi, K ;
Yamaguchi, K ;
Yada, M ;
Tsuji, T ;
Uemura, D .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (04) :771-779
[8]   Absolute configuration of norzoanthamine, a promising candidate for an osteoporotic drug [J].
Kuramoto, M ;
Hayashi, K ;
Fujitani, Y ;
Yamaguchi, K ;
Tsuji, T ;
Yamada, K ;
Ijuin, Y ;
Uemura, D .
TETRAHEDRON LETTERS, 1997, 38 (32) :5683-5686
[9]   DIASTEREOSELECTIVE SYNTHESIS OF CIS-1,2-DIALKENYLCYCLOPROPANOLS AND SUBSEQUENT OXY-COPE REARRANGEMENT [J].
LEE, JH ;
KIM, HJ ;
CHA, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (39) :9919-9920
[10]   Regio- and stereoselectivity in the reductions of cyclic enedione systems [J].
Liu, CJ ;
Burnell, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) :3683-3687