STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-EPIBATIDINE AND (-)-EPIBATIDINE

被引：110

作者：

COREY, EJ

LOH, TP

ACHYUTHARAO, S

DALEY, DC

SARSHAR, S

机构：

[1] Department of Chemistry, Harvard University, Cambridge, Massachusetts

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 21期

关键词：

D O I：

10.1021/jo00073a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereocontrolled total synthesis of the novel analgesic agent (-)-epibatidine (1) and its enantiomer starting with 6-chloropyridine-3-carboxaldehyde (2) has been carried out by way of intermediates 3-10.

引用

页码：5600 / 5602

页数：3

共 7 条

[1] TOTAL SYNTHESIS OF EPIBATIDINE [J].

BROKA, CA .

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

[2] A FACILE SYNTHESIS OF PRIMARY AMINES FROM CARBOXYLIC-ACIDS BY THE CURTIUS REARRANGEMENT [J].

CAPSON, TL ;

POULTER, CD .

TETRAHEDRON LETTERS, 1984, 25 (33) :3515-3518

[3]

CHEN HY, 1993, 205TH ACS NAT M DENV, P347

[4] A VERSATILE TOTAL SYNTHESIS OF EPIBATIDINE AND ANALOGS [J].

HUANG, DF ;

SHEN, TY .

TETRAHEDRON LETTERS, 1993, 34 (28) :4477-4480

[5]

LENZ GR, 1992, CHEMTRACTS ORG CHEM, P332

[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] DIRECT SYNTHESIS OF Z-UNSATURATED ESTERS - A USEFUL MODIFICATION OF THE HORNER-EMMONS OLEFINATION [J].

STILL, WC ;

GENNARI, C .

TETRAHEDRON LETTERS, 1983, 24 (41) :4405-4408

← 1 →