ENANTIOSELECTIVE SYNTHESIS OF 5-SUBSTITUTED-2-FORMYLPYRROLIDINE AND 3,5-DISUBSTITUTED-2-FORMYLPYRROLIDINE DERIVATIVES, THE KEY D-RING FRAGMENTS OF (-)-QUINOCARCIN AND (-)-10-DECARBOXYQUINOCARCIN

被引:40
作者
KATOH, T [1 ]
NAGATA, Y [1 ]
KOBAYASHI, Y [1 ]
ARAI, K [1 ]
MINAMI, J [1 ]
TERASHIMA, S [1 ]
机构
[1] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN
关键词
QUINOCARCIN; 10-DECARBOXYQUINOCARCIN; D-RING FRAGMENT; 5-SUBSTITUTED-2-FORMYLPYRROLIDINE; 3,5-DISUBSTITUTED-2-FORMYLPYRROLIDINE;
D O I
10.1016/S0040-4039(00)73849-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title synthesis was achieved starting from (S)-glutamic acid and (S)-pyroglutamic acid by featuring formation of an N-protected aminal, substitution of the methoxy group with cyanide anion, and reduction of the cyanide to an aldehyde as common key steps.
引用
收藏
页码:5743 / 5746
页数:4
相关论文
共 31 条
[1]  
ALLWAY PA, 1990, TETRAHEDRON LETT, V33, P4781
[2]   ACID AMIDE-REACTIONS L - ORTHO-AMIDES .I. SYNTHESIS AND PROPERTIES OF AMIDE ACETALES AND AMINALESTERS [J].
BREDERECK, H ;
SIMCHEN, G ;
REBSDAT, S ;
KANTLEHNER, W ;
HORN, P ;
WAHL, R ;
HOFFMANN, H ;
GRIESHABER, P .
CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (01) :41-+
[3]   THE TOTAL SYNTHESIS OF QUINOCARCINOL METHYL-ESTER [J].
DANISHEFSKY, SJ ;
HARRISON, PJ ;
WEBB, RR ;
ONEILL, BT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1421-1423
[4]  
FUJIMOTO K, 1987, CANCER RES, V47, P1516
[5]   STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-QUINOCARCIN [J].
FUKUYAMA, T ;
NUNES, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) :5196-5198
[6]   DEVELOPMENT OF AN ASYMMETRIC APPROACH TO THE 3,8-DIAZABICYCLO[3.2.1]OCTANE MOIETY OF QUINOCARCIN VIA INTERMOLECULAR 1,3-DIPOLAR CYCLOADDITIONS OF PHOTOCHEMICALLY GENERATED AZOMETHINE YLIDES [J].
GARNER, P ;
HO, WB ;
GRANDHEE, SK ;
YOUNGS, WJ ;
KENNEDY, VO .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5893-5903
[7]   COMPLEX PYRROLIDINES VIA A TANDEM MICHAEL REACTION/1,3-DIPOLAR CYCLOADDITION SEQUENCE - A NOVEL METHOD FOR THE GENERATION OF UNSYMMETRICAL AZOMETHINE YLIDES [J].
GARNER, P ;
ARYA, F ;
HO, WB .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :412-414
[8]   AN ASYMMETRIC APPROACH TO NAPHTHYRIDINOMYCIN AND QUINOCARCIN VIA A REMARKABLY SELECTIVE INTRAMOLECULAR 1,3-DIPOLAR CYCLO-ADDITION REACTION [J].
GARNER, P ;
SUNITHA, K ;
HO, WB ;
YOUNGS, WJ ;
KENNEDY, VO ;
DJEBLI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09) :2041-2042
[9]   ASYMMETRIC-SYNTHESIS OF (-)-QUINOCARCIN [J].
GARNER, P ;
HO, WB ;
SHIN, HW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2767-2768
[10]   STEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITIONS OF PHOTOCHEMICALLY GENERATED AZOMETHINE YLIDES TO OPPOLZER CHIRAL ACRYLOYL SULTAM - AN ASYMMETRIC APPROACH TO QUINOCARCIN [J].
GARNER, P ;
HO, WB .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :3973-3975