A new route toward 4-substituted pyrazino[2,1-b] qiuinazoline-3,6-dione systems.: Total synthesis of glyantrypine

被引：32

作者：

Cledera, P ^{[1
]}

Avendaño, C ^{[1
]}

Menéndez, JC ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 06期

关键词：

D O I：

10.1021/jo991626e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.

引用

页码：1743 / 1749

页数：7

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