EFFICIENT MICHAEL ADDITION-REACTIONS OF THE N-ARYLSULFONYL-3-PHENYLTHIOPIPERIDONES - SYNTHESIS OF 3-SUBSTITUTED DIHYDROPYRIDINONES

被引:13
作者
NAKAGAWA, M
TORISAWA, Y
HOSAKA, T
TANABE, K
TAVET, F
AIKAWA, M
HINO, T
机构
[1] Faculty of Pharmaceutical Sciences, Chiba University 1-33, Inage-ku, Chiba-shi, 263, Yayoi-cho
关键词
D O I
10.3987/COM-92-S(T)117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient methods for the Michael addition reactions of N-arylsulfonyl-3-phenylthiopiperidones (1) with both the protected amidoacrylates (4, 9) and the simple acrylates (12) have been developed. These reactions offer an efficient route to the 3-alkyl-substituted dihydropyridinones (3, 11), the dienophiles employed in the natural product synthesis.
引用
收藏
页码:1157 / 1170
页数:14
相关论文
共 13 条
[1]   USEFUL DIENE FOR DIELS-ALDER REACTION [J].
DANISHEFSKY, S ;
KITAHARA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7807-7808
[2]  
DANISHEFSKY S, 1990, ORG SYNTH, V7, P312
[3]   INTRAMOLECULAR N-(ACYLOXY)IMINIUM ION ALKYNE CYCLOADDITIONS - A NEW ROUTE TO BICYCLIC ALPHA-AMINO KETONES [J].
FISHER, MJ ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1447-1459
[4]   A DEHYDROALANINE ROUTE TO AN ACTIVATED PHENOLIC SPARSOMYCIN ANALOG [J].
FLYNN, GA ;
BEIGHT, DW .
TETRAHEDRON LETTERS, 1984, 25 (25) :2655-2658
[5]   NEW MANZAMINE ALKALOIDS FROM A SPONGE OF THE GENUS XESTOSPONGIA [J].
ICHIBA, T ;
SAKAI, R ;
KOHMOTO, S ;
SAUCY, G ;
HIGA, T .
TETRAHEDRON LETTERS, 1988, 29 (25) :3083-3086
[6]  
NAKAGAWA M, 1990, HETEROCYCLES, V32, P999
[7]   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
[8]   A CONVENIENT SYNTHESIS OF PROTECTED N-METHYLAMINO ACID DERIVATIVES [J].
OLSEN, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :1912-&
[9]   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
[10]   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