Convergent Strategy to Dizocilpine MK-801 and Derivatives

被引：6

作者：

Reddy, K. Harsha Vardhan ^{[1
]}

Yen-Pon, Expedite ^{[1
]}

Cohen-Kaminsky, Sylvia ^{[2
,3
]}

Messaoudi, Samir ^{[1
]}

Alami, Mouad ^{[1
]}

机构：

[1] Univ Paris Saclay, Univ Paris Sud, Fac Pharm, BioCIS,Lab Chim Therapeut,CNRS, F-92296 Chatenay Malabry, France

[2] Hop Marie Lannelongue, Inserm, UMR S 999, F-92350 Le Plessis Robinson, France

[3] Univ Paris Saclay, Univ Paris Sud, Fac Med, F-94270 Le Kremlin Bicetre, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 07期

关键词：

EFFICIENT; HYDROAMINATION; DEPROTECTION;

D O I：

10.1021/acs.joc.8b00305

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent total synthesis of MK-801 has been achieved. Key synthetic transformations include a multicomponent Barbier-type reaction to construct the alpha-branched amine, a selective Heck alpha-coupling tactic to generate the exocydic alkene skeleton, and a late-stage intramolecular hydroamination reaction between the exocyclic alkene and the secondary protected amine. The efficacy of this method was demonstrated by the synthesis of two news analogues substituted on the aromatic rings.

引用

页码：4264 / 4269

页数：6

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