TOTAL SYNTHESIS OF (-)-NUPHARAMINE AND (+)-3-EPINUPHARAMINE VIA ASYMMETRIC NITROSO DIELS-ALDER REACTION

被引:26
作者
AOYAGI, S
SHISHIDO, Y
KIBAYASHI, C
机构
[1] Tokyo College of Pharmacy, Horinouchi, Hachioji, Tokyo
关键词
D O I
10.1016/S0040-4039(00)92161-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral synthesis of (-)-nupharamine and (+)-3-epinupharamine, based on elaboration of the intramolecular asymmetric Diels-Alder reaction of N-acylnitroso compounds and the introduction of the furyl group in a fully stereocontrolled manner, is described.
引用
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页码:4325 / 4328
页数:4
相关论文
共 12 条
[1]  
ARATA Y, 1957, YAKUGAKU ZASSHI, V77, P792
[2]   SYNTHESIS OF (-)-ALPHA-MULTISTRIATIN [J].
CERNIGLIARO, GJ ;
KOCIENSKI, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (22) :3622-3624
[3]   NUPHAR ALKALOIDS - 3-EPINUPHARAMINE [J].
FORREST, TP ;
RAY, S .
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (10) :1774-&
[4]   STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-)-GEPHYROTOXIN 223AB [J].
IIDA, H ;
WATANABE, Y ;
KIBAYASHI, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5534-5535
[5]  
ITATANI Y, 1976, CHEM PHARM BULL, V24, P2521
[6]   ABSOLUTE CONFIGURATION OF NUPHARAMINE [J].
KAWASAKI, I ;
MATSUTANI, S ;
KANEKO, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1963, 36 (11) :1474-1477
[7]  
OHASHI T, 1959, YAKUGAKU ZASSHI, V79, P734
[8]  
Ohashi T., 1959, YAKUGAKU ZASSHI, V79, P729
[9]  
SABAT M, 1977, Canadian Journal of Chemistry, V55, P3111, DOI 10.1139/v77-436
[10]   CHIRAL SYNTHESIS OF (-)-NUPHARAMINE [J].
SHIMIZU, I ;
YAMAZAKI, H .
CHEMISTRY LETTERS, 1990, (05) :777-778