Synthesis of (±)-aporphine utilizing Pictet-Spengler and intramolecular phenol ortho-arylation reactions

被引：36

作者：

Cuny, GD ^{[1
]}

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 | 2004年 / 45卷 / 26期

关键词：

Pictet-Spengler; palladium; ortho-arylation; phenol; aporphine;

D O I：

10.1016/j.tetlet.2004.04.194

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of the alkaloid (+/-)-aporphine is reported. The initial key step of the synthesis involves a Pictet-Spengler cyclization of N-tosyl tyramine with 2-bromophenylacetaldehyde in trifluoroacetic acid. This step was followed by the second strategic transformation a palladium-mediated intramolecular phenol ortho-arylation reaction utilizing tricyclohexylphosphine as co-catalysts in the presence of cesium carbonate. Finally, de-oxygenation of the phenol, removal of the tosyl group and methylation gave the desired alkaloid.(C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5167 / 5170

页数：4

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