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
[11]  
IMBROSI DO, 1991, TETRAHEDRON LETT, P1815
[12]   PREPARATION OF FREE SULFOXIMINES BY TREATMENT OF N-TOSYLSULFOXIMINES WITH SODIUM ANTHRACENIDE [J].
JOHNSON, CR ;
LAVERGNE, O .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) :986-988
[13]   IRCINAL-A AND IRCINAL-B FROM THE OKINAWAN MARINE SPONGE-IRCINIA SP - PLAUSIBLE BIOGENETIC PRECURSORS OF MANZAMINE ALKALOIDS [J].
KONDO, K ;
SHIGEMORI, H ;
KIKUCHI, Y ;
ISHIBASHI, M ;
SASAKI, T ;
KOBAYASHI, J .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2480-2483
[14]  
LEONARD J, 1992, SYNLETT, P272
[15]  
MARKO IE, 1992, SYNLETT, P275
[16]   SYNTHETIC STUDIES ON MANZAMINE-A .1. DIELS-ALDER REACTION OF 5,6-DIHYDRO-2-PYRIDINONE [J].
NAKAGAWA, M ;
LAI, Z ;
TORISAWA, Y ;
HINO, T .
HETEROCYCLES, 1990, 31 (06) :999-1002
[17]  
NAKAGAWA M, 1993, IN PRESS HETEROCYCLE
[18]   PHYSIOLOGICALLY ACTIVE MARINE NATURAL-PRODUCTS FROM PORIFERA .15. KERAMAMINE-A AND KERAMAMINE-B, NOVEL ANTIMICROBIAL ALKALOIDS FROM THE OKINAWAN MARINE SPONGE PELLINA SP [J].
NAKAMURA, H ;
DENG, SZ ;
KOBAYASHI, J ;
OHIZUMI, Y ;
TOMOTAKE, Y ;
MATSUZAKI, T ;
HIRATA, Y .
TETRAHEDRON LETTERS, 1987, 28 (06) :621-624
[19]   MANZAMINE-A, A NOVEL ANTITUMOR ALKALOID FROM A SPONGE [J].
SAKAI, R ;
HIGA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6404-6405
[20]   MANZAMINE-B AND MANZAMINE-C, 2 NOVEL ALKALOIDS FROM THE SPONGE HALICLONA SP [J].
SAKAI, R ;
KOHMOTO, S ;
HIGA, T .
TETRAHEDRON LETTERS, 1987, 28 (45) :5493-5496