Synthesis of epibatidine homologues: Homoepibatidine and bis-homoepibatidine

被引:50
作者
Malpass, JR
Hemmings, DA
Wallis, AL
机构
[1] Department of Chemistry, University of Leicester
关键词
D O I
10.1016/0040-4039(96)00687-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthetic approaches are described leading to homoepibatidine and bis-homoepibatidine which are based, respectively, on the tropane (8-azabicyclo[3.2.1]octane) and homotropane (9-azabicyclo[4.2.1]nonane) ring systems. Epoxy- tropanes and -homotropanes (which are readily available from simple cyclic dienes) are convenient precursors for the azabicyclic alkenes needed for the key reductive coupling with pyridine derivatives. Copyright (C) 1996 Elsevier Science Ltd
引用
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页码:3911 / 3914
页数:4
相关论文
共 24 条
[1]   N-15 NUCLEAR-MAGNETIC-RESONANCE STUDIES OF AZABICYCLES - UNUSUAL DESHIELDING OF NITROGEN IN THE 7-AZABICYCLO[2.2.1]HEPTYL RING-SYSTEM [J].
BELKACEMI, D ;
DAVIES, JW ;
MALPASS, JR ;
NAYLOR, A ;
SMITH, CR .
TETRAHEDRON, 1992, 48 (46) :10161-10176
[2]   A Meisenheimer rearrangement approach to bridgehead hydroxylated tropane alkaloid derivatives [J].
Bremner, JB ;
Smith, RJ ;
Tarrant, GJ .
TETRAHEDRON LETTERS, 1996, 37 (01) :97-100
[3]   TOTAL SYNTHESIS OF EPIBATIDINE [J].
BROKA, CA .
TETRAHEDRON LETTERS, 1993, 34 (20) :3251-3254
[4]   A TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-EPIBATIDINE [J].
CLAYTON, SC ;
REGAN, AC .
TETRAHEDRON LETTERS, 1993, 34 (46) :7493-7496
[5]  
COREY EJ, 1993, TETRAHEDRON LETT, V34, P4477
[6]   ELECTRONIC CONTROL OF STEREOSELECTIVITY IN THE CHLORINATION OF 1,4-DIHYDRO-1,4-IMINONAPHTHALENES (7-AZABENZONORBORNADIENES) WITH N-CHLOROSUCCINIMIDE [J].
DAVIES, JW ;
DURRANT, ML ;
WALKER, MP ;
MALPASS, JR .
TETRAHEDRON, 1992, 48 (21) :4379-4398
[7]   PREPARATION AND SPECTROSCOPIC STUDIES OF THE 1,4-DIHYDRO-1,4-IMINONAPHTHALENE (7-AZABENZONORBORNADIENE) RING-SYSTEM [J].
DAVIES, JW ;
DURRANT, ML ;
WALKER, MP ;
BELKACEMI, D ;
MALPASS, JR .
TETRAHEDRON, 1992, 48 (05) :861-884
[8]   ISOLATION AND X-RAY STRUCTURE DETERMINATION OF SINGLE INVERTOMERS OF N-CHLOROAMINES [J].
DAVIES, JW ;
MALPASS, JR ;
FAWCETT, J ;
PROUSE, LJS ;
LINDSAY, R ;
RUSSELL, DR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (14) :1135-1137
[9]   SOLVOLYSIS OF N-CHLORO-1,4-DIHYDRO-1,4-IMINONAPHTHALENES(7-AZABENZONORBORNADIENES) - DEPENDENCE OF THE REARRANGEMENT PATHWAY ON THE CONFIGURATION AT NITROGEN [J].
DURRANT, ML ;
MALPASS, JR .
TETRAHEDRON, 1995, 51 (25) :7063-7076
[10]   THE SYNTHESIS OF (+)-EPIBATIDINE AND (-)-EPIBATIDINE [J].
FLETCHER, SR ;
BAKER, R ;
CHAMBERS, MS ;
HOBBS, SC ;
MITCHELL, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (15) :1216-1218