SYNTHESIS OF CHRYSOGINE, A METABOLITE OF PENICILLIUM-CHRYSOGENUM AND SOME RELATED 2-SUBSTITUTED 4-(3H)-QUINAZOLINONES

被引:63
作者
BERGMAN, J
BRYNOLF, A
机构
[1] Department of Organic Chemistry, Royal Institute of Technology
关键词
D O I
10.1016/S0040-4020(01)86694-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Syntheses of both enantiomers of chrysogine, 2-(α-hydroxyethyl)-4(3H)-quinazolinone, 1 from 2-ammobenzamide are reported. Thus reaction of 2-aminobenzamide and optically active α-acetoxypropionyl chloride gave 9, which upon saponification and cyclization induced by aqueous sodium carbonate at room temperature gave chrysogine. The enantiomeric purity of 1 was determined by NMR. Inversion of (-)-(S)-1, using the Mitsunobo reaction, gave (+)- (R)-1. Reduction of 2-acetyl-4(3H)-qumazolinone 2 with baker's yeast gave the S-enantiomer of 1. The cyclization method used could be extended and a number of 2-(α-hydroxy)alkyl-4-(3H)-quinazolinones are also reported. © 1990.
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页码:1295 / 1310
页数:16
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