A short dipolar cycloaddition approach to gamma-lactam alkaloids from Cynometra hankei

被引:44
作者
Fishwick, CWG [1 ]
Foster, RJ [1 ]
Carr, RE [1 ]
机构
[1] GLAXO WELLCOME RES & DEV LTD,MED RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND
关键词
D O I
10.1016/0040-4039(96)00688-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The gamma-lactam based alkaloid cynometrine has been synthesised in four steps from 1-methyl-imidazole-4-carboxaldehyde. The key step involves an efficient regio-, stereo-, and chemoselective 1,3-dipolar cycloaddition of a dithiolane-fused azomethine ylide. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:3915 / 3918
页数:4
相关论文
共 11 条
[1]  
BUCHANAN RM, 1994, INORG CHEM, V33, P2376
[2]   Hetero-1,3-dipolar cycloadditions of dithiolane-isocyanate iminium methylides: A novel route to 1,3-oxazolidine- and thiazolidine-2-thiones [J].
Fishwick, CWG ;
Foster, RJ ;
Carr, RE .
TETRAHEDRON LETTERS, 1996, 37 (05) :711-714
[3]   Dithiolane-isocyanate imminium methylides: A rapid stereoselective entry into gamma-lactams [J].
Fishwick, CWG ;
Foster, RJ ;
Carr, RE .
TETRAHEDRON LETTERS, 1995, 36 (51) :9409-9412
[4]  
GIMMETT MR, 1970, ADV HET CHEM, V12, P103
[5]  
HENNART JAA, Patent No. 2307867
[6]  
KHUONGHUU F, 1982, TETRAHEDRON, V38, P2687
[7]  
MONSEUR X, 1973, TETRAHEDRON LETT, P1757
[9]   DIASTEREOSELECTIVITY IN THE BORANATE REDUCTION OF ALPHA-TRIAZOLYL KETONES [J].
THIEME, PC ;
SAUTER, H ;
REISSENWEBER, G .
CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (06) :1059-1062
[10]   IMIDAZOLE ALKALOIDS FROM CYNOMETRA-HANKEI [J].
WATERMAN, PG ;
FAULKNER, DF .
PHYTOCHEMISTRY, 1981, 20 (12) :2765-2767