INTRAMOLECULAR PICTET-SPENGLER REACTION OF N-ALKOXYTRYPTOPHANS AND TRYPTAMINES .2. SYNTHESIS OF CORYNANTHE ALKALOID DERIVATIVES CONTAINING A TETRAHYDRO-1,2-OXAZINE AS THE D-RING

被引：25

作者：

HERMKENS, PHH

VONMAARSEVEEN, JH

BERENS, HW

SMITS, JMM

KRUSE, CG

SCHEEREN, HW

机构：

[1] CATHOLIC UNIV NIJMEGEN,DEPT ORGAN CHEM,6525 ED NIJMEGEN,NETHERLANDS

[2] DUPHAR RES LABS,1380 AA WEESP,NETHERLANDS

[3] CATHOLIC UNIV NIJMEGEN,DEPT CRYSTALLOG,6525 ED NIJMEGEN,NETHERLANDS

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 07期

关键词：

D O I：

10.1021/jo00294a041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-hydroxtryptamines 1–3 were converted into the N-alkoxy derivatives 26–29 by successive protection with 2-(trimethylsilyl)ethyl chloroformate providing 19–21, reaction with functionalized alkylhalides, and de-protection with tetrabutylammonium fluoride. Intramolecular cyclization of 26–29 under acidic or reductive conditions gave the corynanthe analogues 4–6 in good yields. © 1990, American Chemical Society. All rights reserved.

引用

页码：2200 / 2206

页数：7

共 51 条

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