Short stereocontrolled synthesis of trans and cis-tetrahydro-pyrazinoisoquinolinediones

被引：19

作者：

González, JF ^{[1
]}

de la Cuesta, E ^{[1
]}

Avendaño, C ^{[1
]}

机构：

[1] Univ Complutense Madrid, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(03)00897-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of aldehyde dimethyl acetals (here acetaldehyde) to unisolated O-trimethylsilyl derivatives of 1-acetyl-3-aryl-methylpiperazine-2,5-diones (here 2,5-dimethoxyphenyl), in the presence of TMSOTf as the catalyst, gave nearly quantitatively the corresponding N-methoxyalkyl derivatives which, under acidic treatment, gave in very good yield through a Pictet-Spengler-type reaction involving N-acyliminium cations (6S*,11aR*)-2-acetyl-6-alkyl-3,6,11,11a-tetrahydro-2H-pyrazino[1,2-b]isoquinoline-1,4-diones. Epimerization of the 11a-stereocentre was accomplished by radical bromination, spontaneous hydrobromide elimination and catalytic hydrogenation, to give the (6S*,11aS*)-isomers. We propose these compounds as precursors of tetrahydroisoquinoline antitumour antibiotics. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4395 / 4398

页数：4

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