Total synthesis of nigellicine and nigeglanine hydrobromide

被引:34
作者
Elliott, EL [1 ]
Bushell, SM [1 ]
Cavero, M [1 ]
Tolan, B [1 ]
Kelly, TR [1 ]
机构
[1] Boston Coll, EF Merkert Chem Ctr, Chestnut Hill, MA 02467 USA
关键词
D O I
10.1021/ol050769m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The first syntheses of the pyridazinoindazolium alkaloids nigellicine and nigeglanine hydrobromide via a common intermediate are described. Ortho-lithiation/acylation and the direct amination of an isatin ring system are the key steps in the synthesis.
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页码:2449 / 2451
页数:3
相关论文
共 19 条
[1]   DETERMINATION OF ABSOLUTE STRUCTURE OF (-)-OUDEMANSIN-B [J].
AKITA, H ;
MATSUKURA, H ;
OISHI, T .
TETRAHEDRON LETTERS, 1986, 27 (44) :5397-5400
[2]   ISOLATION AND STRUCTURE DETERMINATION OF NIGELLICINE, A NOVEL ALKALOID FROM THE SEEDS OF NIGELLA-SATIVA [J].
ATTAURRAHMAN ;
MALIK, S ;
HE, CH ;
CLARDY, J .
TETRAHEDRON LETTERS, 1985, 26 (23) :2759-2762
[3]   NIGELLIDINE - A NEW INDAZOLE ALKALOID FROM THE SEEDS OF NIGELLA-SATIVA [J].
ATTAURRAHMAN ;
MALIK, S ;
HASAN, SS ;
CHOUDHARY, MI ;
NI, CZ ;
CLARDY, J .
TETRAHEDRON LETTERS, 1995, 36 (12) :1993-1996
[4]  
Behr L. C., 1967, CHEM HETEROCYCLIC CO, V22
[5]  
Borsche W, 1934, LIEBIGS ANN CHEM, V510, P287
[6]   INDAZOLE-3-CARBOXYLIC ACIDS AND THEIR DERIVATIVES [J].
BUUHOI, NP ;
HOEFFINGER, JP ;
JACQUIGNON, P .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1964, 1 (05) :239-+
[8]  
CHUGAI PHARM CO LTD, 1985, Patent No. 60004185
[9]   SYNTHESIS AND PHARMACOLOGICAL CHARACTERIZATION OF 2-(4-CHLORO-3-HYDROXYPHENYL)ETHYLAMINE AND N,N-DIALKYL DERIVATIVES AS DOPAMINE RECEPTOR LIGANDS [J].
CLAUDI, F ;
GIORGIONI, G ;
DISTEFANO, A ;
ABBRACCHIO, MP ;
PAOLETTI, AM ;
BALDUINI, W .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (23) :4408-4414
[10]  
COLEMAN GH, 1964, ORG SYNTH, V1, P442