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

页码：8149 / 8152

页数：4

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