ENANTIOSELECTIVE TOTAL SYNTHESIS OF GLYOXALASE I INHIBITOR USING ASYMMETRIC DIELS-ALDER REACTION OF A NEW CHIRAL DIENOPHILE, (S)S-3-(3-TRIFLUOROMETHYLPYRID-2-YLSULFINYL)ACRYLATE

被引:71
作者
TAKAYAMA, H [1 ]
HAYASHI, K [1 ]
KOIZUMI, T [1 ]
机构
[1] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,SUGITANI 2630,SUGITANI,TOYAMA 93001,JAPAN
关键词
D O I
10.1016/S0040-4039(00)85252-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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页码:5509 / 5512
页数:4
相关论文
共 13 条
[1]   OPTICALLY-ACTIVE 2-PARA-TOLYLSULFINYLACRYLATE - A NOVEL CHIRAL DIENOPHILE WHICH EXHIBITS HIGH REACTIVITY AND DIASTEREOSELECTIVITY [J].
ARAI, Y ;
KUWAYAMA, S ;
TAKEUCHI, Y ;
KOIZUMI, T .
TETRAHEDRON LETTERS, 1985, 26 (50) :6205-6208
[2]   STRUCTURE OF A GLYOXALASE-I INHIBITOR AND ITS CHEMICAL REACTIVITY WITH SH-COMPOUNDS [J].
CHIMURA, H ;
NAKAMURA, H ;
TAKITA, T ;
TAKEUCHI, T ;
UMEZAWA, H ;
KATO, K ;
SAITO, S ;
TOMISAWA, T ;
IITAKA, Y .
JOURNAL OF ANTIBIOTICS, 1975, 28 (10) :743-748
[3]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[4]   CHEMICAL BASIS OF THE ACTION OF GLYOXALASE-I, AN ANTICANCER TARGET ENZYME [J].
DOUGLAS, KT ;
SHINKAI, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1985, 24 (01) :31-44
[5]  
ICHIHARA A, 1976, TETRAHEDRON LETT, P4741
[6]   HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTION OF OPTICALLY-ACTIVE ETHYL 2-PARA-TOLYLSULFINYLMETHYLENEPROPIONATE WITH CYCLOPENTADIENE [J].
KOIZUMI, T ;
HAKAMADA, I ;
YOSHII, E .
TETRAHEDRON LETTERS, 1984, 25 (01) :87-90
[7]   SYNTHESIS OF A GLYOXALASE-I INHIBITOR FROM STREPTOMYCES-GRISEOSPOREUS NIIDA ET OGASAWARA [J].
MIRZA, S ;
MOLLEYRES, LP ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1985, 68 (04) :988-996
[8]  
MISLOW K, 1965, J AM CHEM SOC, V87, P1958
[9]   PENEMS, A NEW CLASS OF BETA-LACTAM ANTIBIOTICS .4. SYNTHESES OF RACEMIC AND ENANTIOMERIC PENEM CARBOXYLIC-ACIDS [J].
PFAENDLER, HR ;
GOSTELI, J ;
WOODWARD, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (21) :6306-6310
[10]   MECHANISM OF ACTION OF 2-CROTONYLOXYMETHYL-4,5,6-TRIHYDROXYCYCLOHEX-2-ENONE, A SH INHIBITORY ANTI-TUMOR ANTIBIOTIC, AND ITS EFFECT ON DRUG-RESISTANT NEOPLASTIC-CELLS [J].
SUGIMOTO, Y ;
SUZUKI, H ;
YAMAKI, H ;
NISHIMURA, T ;
TANAKA, N .
JOURNAL OF ANTIBIOTICS, 1982, 35 (09) :1222-1230