A practical enantioselective synthesis of Epibatidine

被引：39

作者：

Szantay, C

KardosBalogh, Z

Moldvai, I

Szantay, C

TemesvariMajor, E

Blasko, G

机构：

[1] GEDEON RICHTER CHEM WORKS LTD,CHEM WORKS,SPECTROSCOP RES DIV,H-1475 BUDAPEST,HUNGARY

[2] EGIS PHARMACEUT,H-1475 BUDAPEST,HUNGARY

来源：

TETRAHEDRON | 1996年 / 52卷 / 33期

关键词：

D O I：

10.1016/0040-4020(96)00623-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two different syntheses of Epibatidine (1) were designed and carried out using easily accessible reagents and convenient reaction conditions. The ring closure of the prochiral precursor 4 catalyzed by optically active alpha-phenyl-ethyl-amine gave the key intermediate 5 in over 80% ee from which the natural product (-)-1 has been prepared. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：11053 / 11062

页数：10

共 33 条

[1] TOTAL SYNTHESIS OF (+/-)-EPIBATIDINE
ALBERTINI, E
BARCO, A
BENETTI, S
DERISI, C
POLLINI, GP
ROMAGNOLI, R
ZANIRATO, V
[J]. TETRAHEDRON LETTERS, 1994, 35 (49) : 9297 - 9300
[2] ANDERSON DJ, 1995, J PHARMACOL EXP THER, V273, P1434
[3] IS EPIBATIDINE REALLY ANALGESIC - DISSOCIATION OF THE ACTIVITY, TEMPERATURE, AND ANALGESIC EFFECTS OF(+/-)-EPIBATIDINE
BANNON, AW
GUNTHER, KL
DECKER, MW
[J]. PHARMACOLOGY BIOCHEMISTRY AND BEHAVIOR, 1995, 51 (04) : 693 - 698
[4] THE INFLUENCE OF BAY K-8644 TREATMENT ON (+/-)-EPIBATIDINE-INDUCED ANALGESIA
BANNON, AW
GUNTHER, KL
DECKER, MW
ARNERIC, SP
[J]. BRAIN RESEARCH, 1995, 678 (1-2) : 244 - 250
[5] Bejeuhr G, 1994, Pharm Unserer Zeit, V23, P105, DOI 10.1002/pauz.19940230210
[6] BOHAUS DW, 1995, J PHARMACOL EXP THER, V272, P1199
[7] HUMAN ALPHA-7 NICOTINIC ACETYLCHOLINE-RECEPTOR RESPONSES TO NOVEL LIGANDS
BRIGGS, CA
MCKENNA, DG
PIATTONIKAPLAN, M
[J]. NEUROPHARMACOLOGY, 1995, 34 (06) : 583 - 590
[8] TOTAL SYNTHESIS OF EPIBATIDINE
BROKA, CA
[J]. TETRAHEDRON LETTERS, 1993, 34 (20) : 3251 - 3254
[9] A TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-EPIBATIDINE
CLAYTON, SC
REGAN, AC
[J]. TETRAHEDRON LETTERS, 1993, 34 (46) : 7493 - 7496
[10] STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-EPIBATIDINE AND (-)-EPIBATIDINE
COREY, EJ
LOH, TP
ACHYUTHARAO, S
DALEY, DC
SARSHAR, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) : 5600 - 5602

← 1 2 3 4 →