THE SYNTHESIS OF (+)-EPIBATIDINE AND (-)-EPIBATIDINE

被引：71

作者：

FLETCHER, SR ^{[1
]}

BAKER, R ^{[1
]}

CHAMBERS, MS ^{[1
]}

HOBBS, SC ^{[1
]}

MITCHELL, PJ ^{[1
]}

机构：

[1] MERCK SHARP & DOHME LTD,NEUROSCI RES CTR,TERLINGS PK,EASTWICK RD,HARLOW CM20 2QR,ESSEX,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 15期

关键词：

D O I：

10.1039/c39930001216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of the alkaloid epibatidine {exo-2-(2-chloro-5-pyridyl)-7-azabicyclo[2.2,1]heptane} in enantiomeric form involving, as the critical step, reaction or 5-lithio-2-chloropyridine with N-tert-butoxycarbonyl-7-azabicyclo[2.2.1]heptan-2-one is described.

引用

页码：1216 / 1218

页数：3

共 7 条

[1]

[Anonymous], COMMUNICATION

[2] TOTAL SYNTHESIS OF EPIBATIDINE [J].

BROKA, CA .

TETRAHEDRON LETTERS, 1993, 34 (20) :3251-3254

[3]

MAGIDSON O, 1925, CHEM BER, V58, P113

[4] SYNTHESIS AND BRONCHODILATOR ACTIVITY OF ENDO-2-(2-CYCLOPENTYL-2-HYDROXY-2-PHENYL)ACETOXY-7-METHYL-7-AZABICYCLO-[2.2.1]HEPTANE METHOBROMIDE, A POTENT AND LONG-ACTING ANTICHOLINERGIC AGENT [J].

PFISTER, JR ;

WYMANN, WE ;

WEISSBERG, RM ;

STROSBERG, AM .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1985, 74 (02) :208-210

[5]

PFISTER JR, 1983, SYNTHESIS-STUTTGART, P38

[6] EPIBATIDINE - A NOVEL (CHLOROPYRIDYL)AZABICYCLOHEPTANE WITH POTENT ANALGESIC ACTIVITY FROM AN ECUADORIAN POISON FROG [J].

SPANDE, TF ;

GARRAFFO, HM ;

EDWARDS, MW ;

YEH, HJC ;

PANNELL, L ;

DALY, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (09) :3475-3478

[7]

1924, Patent No. 491681

← 1 →