A NOVEL EFFICIENT SYNTHESIS OF 1-ETHOXYVINYL ESTERS AND THEIR USE IN ACYLATION OF AMINES AND ALCOHOLS - SYNTHESIS OF WATER-SOLUBLE OXAUNOMYCIN DERIVATIVES

被引:0
作者
KITA, Y
MAEDA, H
OMORI, K
OKUNO, T
TAMURA, Y
机构
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
I-Ethoxyvinyl esters (la-i), prepared by the addition of carboxylic acids to ethoxyacetylene in the presence of a catalytic amount of [RuCl2(p-cymene)]2, react with amines (3a-d) and alcohols (5a-e) to give the corresponding N- and 0-acylated compounds (4a-1 and 6a-f) in high yields. Application of this method to the synthesis of water-soluble oxaunomycin derivatives (9a,b) is also described.
引用
收藏
页码:273 / 274
页数:2
相关论文
共 15 条
[1]   RUTHENIUM-CATALYZED ADDITIONS TO ALKYNES - SYNTHESIS OF ACTIVATED ESTERS AND THEIR USE IN ACYLATION REACTIONS [J].
BRUNEAU, C ;
NEVEUX, M ;
KABOUCHE, Z ;
RUPPIN, C ;
DIXNEUF, PH .
SYNLETT, 1991, (11) :755-763
[2]   ENOL ESTERS AS INTERMEDIATES FOR THE FACILE CONVERSION OF AMINO-ACIDS INTO AMIDES AND DIPEPTIDES [J].
KABOUCHE, Z ;
BRUNEAU, C ;
DIXNEUF, PH .
TETRAHEDRON LETTERS, 1991, 32 (39) :5359-5362
[3]   THE 1ST TOTAL SYNTHESIS OF A POTENT BETA-RHODOMYCIN, OXAUNOMYCIN - REGIOSELECTIVE GLYCOSIDATION OF THE C-7 HYDROXYL GROUP OF BETA-RHODOMYCINONE [J].
KITA, Y ;
MAEDA, H ;
KIRIHARA, M ;
FUJII, Y ;
NAKAJIMA, T ;
YAMAMOTO, H ;
FUJIOKA, H .
TETRAHEDRON LETTERS, 1990, 31 (49) :7173-7174
[4]  
KITA Y, 1992, CHEM PHARM BULL, V40, P61
[5]   FACILE AND EFFICIENT SYNTHESES OF CARBOXYLIC ANHYDRIDES AND AMIDES USING (TRIMETHYLSILYL)ETHOXYACETYLENE [J].
KITA, Y ;
AKAI, S ;
AJIMURA, N ;
YOSHIGI, M ;
TSUGOSHI, T ;
YASUDA, H ;
TAMURA, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) :4150-4158
[6]   RUTHENIUM COMPLEX CATALYZED SELECTIVE ADDITION OF CARBOXYLIC-ACIDS TO ACETYLENES GIVING ENOL ESTERS [J].
MITSUDO, T ;
HORI, Y ;
YAMAKAWA, Y ;
WATANABE, Y .
TETRAHEDRON LETTERS, 1986, 27 (19) :2125-2126
[7]   SELECTIVE ADDITION OF UNSATURATED CARBOXYLIC-ACIDS TO TERMINAL ACETYLENES CATALYZED BY BIS(ETA-5-CYCLOOCTADIENYL)RUTHENIUM(II)-TRI-NORMAL-BUTYL-PHOSPHINE - A NOVEL SYNTHESIS OF ENOL ESTERS [J].
MITSUDO, T ;
HORI, Y ;
WATANABE, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1566-1568
[8]   RUTHENIUM-CATALYZED SELECTIVE ADDITION OF CARBOXYLIC-ACIDS TO ALKYNES - A NOVEL SYNTHESIS OF ENOL ESTERS [J].
MITSUDO, T ;
HORI, Y ;
YAMAKAWA, Y ;
WATANABE, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) :2230-2239
[9]   ENOL FORMATES - RUTHENIUM CATALYZED FORMATION AND FORMYLATING REAGENTS [J].
NEVEUX, M ;
BRUNEAU, C ;
DIXNEUF, PH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05) :1197-1199
[10]   ADDITION OF CARBOXYLIC-ACIDS TO ALKYNES CATALYZED BY RUTHENIUM COMPLEXES - VINYL ESTER FORMATION [J].
ROTEM, M ;
SHVO, Y .
ORGANOMETALLICS, 1983, 2 (11) :1689-1691