Tandem N-acyliminium/Pictet-Spengler/intramolecular Diels-Alder reaction:: an expedient route to hexacyclic tetrahydro-β-carbolines

被引：44
作者：
Paulvannan, K [1 ]
Hale, R [1 ]
Mesis, R [1 ]
Chen, T [1 ]
机构：
[1] Affymax Res Inst, Santa Clara, CA 95051 USA
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 02期
关键词：
D O I：
10.1016/S0040-4039(01)02074-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild and efficient synthesis of rigid hexacyclic nitrogen heterocycles with tetrahydro-beta-carboline skeleton is described. Acylation of the imines 7a-d, prepared from tryptamine (5) and furaldehydes 6a-d, with maleic anhydride at room temperature provided the corresponding hexacyclic nitrogen heterocycles 10a-d via a tandem N-acyliminium/Pictet-Spengler/IMDA reaction. In this tandem approach, five stereocenters, including a quaternary center and three rings are generated with excellent stereoselectivity. Key to the success of this approach, is the use of furaldehyde and maleic anhydride as the aldehyde and anhydride components, respectively. Transformation of the free acid to the corresponding amide, ester and alcohol is also studied. (C) 2002 Elsevier Science Ltd. All rights reserved.
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页码：203 / 207
页数：5
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