The aza-xylylene Diels-Alder approach for the synthesis of naturally occurring 2-alkyl tetrahydroquinolines

被引：62
作者：
Avemaria, F
Vanderheiden, S
Bräse, S
机构：
[1] Univ Karlsruhe, Inst Organ Chem, D-76131 Karlsruhe, Germany
[2] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
来源：
TETRAHEDRON | 2003年 / 59卷 / 35期
关键词：
tetrahydroquinolines; aza-xylylene; Diels-Alder reaction;
D O I：
10.1016/S0040-4020(03)00915-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The recently discovered intramolecular aza-xylylene Diels-Alder reaction, based on a 1,4-dehydrohalogenation reaction, was extended in terms of substrates and leaving groups allowing the assembly of tetrahydroquinolines in two synthetic steps. Intramolecular cleavage of a thiocarbamate using triphenylphosphine and tetrachloromethane (Appel conditions) to give chloromethyl phenylisocyanate has been presented for the first time. The synthetic feasibility of this process was demonstrated in the first total syntheses of the alkaloids rac-Angustureine and 1-methyl-2-propyltetrahydroquinoline. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6785 / 6796
页数：12
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