Intramolecular ortho-arylation of phenols utilized in the synthesis of the aporphine alkaloids (±)-lirinidine and (±)-nuciferine

被引：39
作者：
Cuny, GD
机构：
[1] Brigham & Womens Hosp, Lab Drug Discovery Neurodegenerat, Cambridge, MA 02139 USA
[2] Harvard Univ, Sch Med, Cambridge, MA 02139 USA
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 44期
关键词：
palladium; ortho-arylation; phenol; aporphine; lirinidine; nuciferine;
D O I：
10.1016/j.tetlet.2003.09.026
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-mediated intramolecular phenol ortho-arylation reaction applied to the construction of aporphine alkaloids is reported. Most significantly, the efficiency of this transformation was enhanced by the utilization of trialkylphosphine (i.e. tricyclohexylphosphine) or trialkylphosphonium salts (i.e. di-tert-butylmethyl-phosphonium tetrafluoroborate) as co-catalysts in the presence of cesium carbonate. This methodology was employed in the syntheses of the aporphine alkaloids (+/-)-lirinidine and (+/-)-nuciferine. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8149 / 8152
页数：4
相关论文
共 42 条
[1]   INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].
ABELMAN, MM ;
OH, T ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4130-4133
[2]   Oral treatment of erectile dysfunction with apomorphine SL [J].
Altwein, JE ;
Keuler, FU .
UROLOGIA INTERNATIONALIS, 2001, 67 (04) :257-263
[3]   The catalytic intermolecular orthoarylation of phenols [J].
Bedford, RB ;
Coles, SJ ;
Hursthouse, MB ;
Limmert, ME .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) :112-114
[4]   SRN1 STUDIES .26. SRN1-BASED METHODOLOGY FOR SYNTHESIS OF NAPHTHYLQUINOLINES AND NAPHTHYLISOQUINOLINES [J].
BEUGELMANS, R ;
BOISCHOUSSY, M .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2518-2522
[5]   SRN1 STUDIES .27. SYNTHESIS OF FLUORINATED BIARYL DERIVATIVES VIA SRN1 REACTIONS [J].
BEUGELMANS, R ;
CHASTANET, J .
TETRAHEDRON LETTERS, 1991, 32 (29) :3487-3490
[6]  
BEUGELMANS R, 1993, HETEROCYCLES, V36, P2723
[7]   First total synthesis of the 7,3′-linked naphthylisoquinoline alkaloid ancistrocladidine [J].
Bungard, CJ ;
Morris, JC .
ORGANIC LETTERS, 2002, 4 (04) :631-633
[8]   HECK REACTION ON ANTHRAQUINONE DERIVATIVES - LIGAND, SOLVENT, AND SALT EFFECTS [J].
CABRI, W ;
CANDIANI, I ;
DEBERNARDINIS, S ;
FRANCALANCI, F ;
PENCO, S ;
SANTI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5796-5800
[9]   ISOQUINOLINE ALKALOIDS .16. THE DEMETHYLATION OF APORPHINES WITH SULFURIC-ACID [J].
CASTEDO, L ;
LERA, ARD ;
SAA, JM ;
SUAU, R ;
VILLAVERDE, C .
HETEROCYCLES, 1980, 14 (08) :1135-1138
[10]   The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst [J].
Dai, CY ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2719-2724
12345