DIHYDROPYRIDINONE APPROACH TO MANZAMINES - AN EXPEDIENT CONSTRUCTION OF THE TETRACYCLIC CORE OF MANZAMINE-A

被引:47
作者
NAKAGAWA, M [1 ]
TORISAWA, Y [1 ]
HOSAKA, T [1 ]
TANABE, K [1 ]
DATE, T [1 ]
OKAMURA, K [1 ]
HINO, T [1 ]
机构
[1] TANABE SEIYAKU CO LTD,ORGAN CHEM RES LAB,TODA,SAITAMA 335,JAPAN
关键词
D O I
10.1016/0040-4039(93)88081-S
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A construction of the central tetracyclic core (19) of manzamine A (1) was successfully achieved by a highly efficient Diels-Alder reaction of the suitably protected dihydropyridinones (5) and Danishefsky's diene as a key strategy. Expedient conversion of the D-A product (7) to the precursor (15) was followed by the azocine lactam ring closure to furnish the titled core.
引用
收藏
页码:4543 / 4546
页数:4
相关论文
共 23 条
[1]   ON THE BIOSYNTHESIS OF MANZAMINES [J].
BALDWIN, JE ;
WHITEHEAD, RC .
TETRAHEDRON LETTERS, 1992, 33 (15) :2059-2062
[2]   SYNTHESIS OF THE TRICYCLIC HEART OF MANZAMINES [J].
BRANDS, KMJ ;
PANDIT, UK .
TETRAHEDRON LETTERS, 1989, 30 (11) :1423-1426
[3]  
BRANDS KMJ, 1990, HETEROCYCLES, V30, P257
[4]   SYNTHESIS OF THE HOMOCHIRAL TRICYCLIC HEART OF MANZAMINE-A [J].
BRANDS, KMJ ;
MEEKEL, AAP ;
PANDIT, UK .
TETRAHEDRON, 1991, 47 (10-11) :2005-2026
[5]   SYNTHESIS OF A TETRACYCLIC SUBSTRUCTURE OF MANZAMINE-A [J].
CAMPBELL, JA ;
HART, DJ .
TETRAHEDRON LETTERS, 1992, 33 (42) :6247-6250
[6]   MEDIUM RING NITROGEN-HETEROCYCLES [J].
EVANS, PA ;
HOLMES, AB .
TETRAHEDRON, 1991, 47 (44) :9131-9166
[7]  
HAMADA Y, 1985, TETRAHEDRON LETT, V42, P5155
[8]   SYNTHESIS OF THE PYRROLO[2,3-I]ISOQUINOLINE SUBSTRUCTURE OF THE MANZAMINE FAMILY OF ALKALOIDS [J].
HART, DJ ;
MCKINNEY, JA .
TETRAHEDRON LETTERS, 1989, 30 (20) :2611-2614
[9]  
ICHIBA T, 1988, TETRAHEDRON LETT, V29, P3283
[10]  
IMBROISI DD, 1989, TETRAHEDRON LETT, V30, P4309