SYNTHETIC STUDIES ON TAUTOMYCIN SYNTHESIS OF 2,3-DISUBSTITUTED MALEIC-ANHYDRIDE SEGMENT

被引:35
作者
NAGANAWA, A [1 ]
ICHIKAWA, Y [1 ]
ISOBE, M [1 ]
机构
[1] NAGOYA UNIV,SCH AGR SCI,ORGAN CHEM LAB,CHIKUSA KU,NAGOYA 46401,JAPAN
关键词
D O I
10.1016/S0040-4020(01)85365-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 2,3-disubstituted maleic anhydride segment of tautomycin has been synthesized in optically active form. Oxidation of 3,4-disubsrituted furan employing singlet oxygen completes the construction of the maleic anhydride moiety. Esterification of the maleic anhydride segment without protecting anhydride moiety resulted in the successful coupling reaction with fragment derived from tautomycin.
引用
收藏
页码:8969 / 8982
页数:14
相关论文
共 24 条
[1]  
CHENG XC, 1990, J ANTIBIOT, V43, P809, DOI 10.7164/antibiotics.43.809
[2]   A NEW ANTIBIOTIC, TAUTOMYCIN [J].
CHENG, XC ;
KIHARA, T ;
KUSAKABE, H ;
MAGAE, J ;
KOBAYASHI, Y ;
FANG, RP ;
NI, ZF ;
SHEN, YC ;
KO, K ;
YAMAGUCHI, I ;
ISONO, K .
JOURNAL OF ANTIBIOTICS, 1987, 40 (06) :907-909
[3]   TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC CYTOVARICIN [J].
EVANS, DA ;
KALDOR, SW ;
JONES, TK ;
CLARDY, J ;
STOUT, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7001-7031
[4]   ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
BARTROLI, J ;
SHIH, TL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129
[5]  
GAGE JR, 1993, ORG SYNTH, V8, P528
[6]   A STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED MALEIC ESTERS BY USE OF PHOSPHONATES [J].
HUFF, RK ;
MOPPETT, CE ;
SUTHERLA.JK .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (22) :2725-&
[7]   NONADRIDES .6. DIMERIZATION OF C-9 UNIT IN-VIVO AND IN-VITRO [J].
HUFF, RK ;
SUTHERLA.JK ;
MOPPETT, CE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (20) :2584-&
[8]   SYNTHESIS OF 3,4-BIS-ACETOXYMETHYL-FURAN [J].
HUTTON, J ;
POTTS, B ;
SOUTHERN, PF .
SYNTHETIC COMMUNICATIONS, 1979, 9 (09) :789-797
[9]  
ICHIKAWA Y, 1993, SYNLETT, P907
[10]   CONFIRMATION OF THE RELATIVE STEREOCHEMISTRY AT C-23 AND C-24 OF TAUTOMYCIN [J].
ICHIKAWA, Y ;
ISOBE, M ;
UBUKATA, M ;
ISONO, K .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1993, 57 (08) :1382-1383