NEW SYNTHESIS OF ORELLINE BY METALATION OF METHOXYPYRIDINES

被引：50

作者：

TRECOURT, F ^{[1
]}

MALLET, M ^{[1
]}

MONGIN, O ^{[1
]}

GERVAIS, B ^{[1
]}

QUEGUINER, G ^{[1
]}

机构：

[1] INST NATL SCI APPL ROUEN,IRCOF,URA 1429,CHIM ORGAN FINE & HETEROCYCL LAB,BP 08,F-76131 MONT ST AIGNAN,FRANCE

来源：

TETRAHEDRON | 1993年 / 49卷 / 37期

关键词：

ALKALOIDS; ALKOXYPYRIDINES; COUPLING; METALATION; ORELLINE;

D O I：

10.1016/S0040-4020(01)81920-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new total synthesis in five steps of the alkaloid Orelline is reported. The methodology of methoxypyridines to afford 2-halo-3,4-dimethoxypyridine on which an homocoupling reaction is performed to but the 2,2'-bipyridyl structure of the alkaloid.

引用

页码：8373 / 8380

页数：8

共 21 条

[1]

ANTKOWIAK WZ, 1979, TETRAHEDRON LETT, V21, P1931

[2] N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - SYNTHESIS OF (+/-)-SEPTICINE AND (+/-)-TYLOPHORINE [J].

COMINS, DL ;

MORGAN, LA .

TETRAHEDRON LETTERS, 1991, 32 (42) :5919-5922

[3] ORTHO LITHIATION OF 2-METHOXYPYRIDINES, 3-METHOXYPYRIDINES, AND 4-METHOXYPYRIDINES [J].

COMINS, DL ;

LAMUNYON, DH .

TETRAHEDRON LETTERS, 1988, 29 (07) :773-776

[4] THE SYNTHESIS OF [C-14] PANTOPRAZOLE - SK-AND-F 96022Z - AN H+/K+ ATPASE INHIBITOR [J].

CROWE, AM ;

JOHNSTON, CEA ;

LAWRIE, KWM ;

SAUNDERS, D .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1992, 31 (05) :409-416

[5]

DEHMLOW EV, 1987, LIEBIGS ANN CHEM, P857, DOI 10.1002/jlac.198719870840

[6] SYNTHESIS OF ORELLANINE, THE LETHAL POISON OF A TOADSTOOL [J].

DEHMLOW, EV ;

SCHULZ, HJ .

TETRAHEDRON LETTERS, 1985, 26 (40) :4903-4906

[7] IMPROVED METALATION OF 2,4,6-TRIBROMOANISOLE - SYNTHESIS OF 2-METHOXYRESORCINOL [J].

GREEN, K .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4325-4326

[8] SYNTHESIS OF ORELLINE [J].

HASSEBERG, HA ;

GERLACH, H .

HELVETICA CHIMICA ACTA, 1988, 71 (05) :957-963

[9]

KLEIPOOL RJC, 1950, RECL TRAV CHIM PAY B, V69, P37

[10] PHENYLLITHIUM - NEW AGENT FOR METALATION OF THE PYRIDINE RING [J].

MALLET, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 406 (1-2) :49-56

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