AMINO-ACIDS .15. SYNTHESIS OF ENANTIOPURE DAVA-DERIVATIVES (5-AMINO-4-HYDROXYPENTANOIC ACIDS) FROM (S)-GLUTAMIC ACID

被引：3
作者：
HERDEIS, C
LUTSCH, K
WAIBEL, D
机构：
[1] Institut für Pharmazie und Lebensmittelchemie, Universität Würzburg, Würzburg, D-97074, Am Hubland
来源：
ARCHIV DER PHARMAZIE | 1994年 / 327卷 / 01期
关键词：
D O I：
10.1002/ardp.19943270108
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Starting from (S)-glutamic acid the readily available hydroxymethyl lactone 1 is protected as the TBDPS ether 2. Alkylation of the lithium enolate of 2 provides the lactones 3a,b with high diastereomeric excess. On the other hand 1,4 addition of Gilman cuprates to 10 furnishes the alcohols 12a,b after deprotection. Transformation of 4,12 via the mesylates 5,13 and the azides 6,14 affords the Boc protected amines 7,15 after catalytic hydrogenation in the presence of Boc2O. After treatment of 7,15 with methanolic HCI the rings of the crystalline hydrochlorides 8,16 are opened to the DAVA-derivatives (delta-aminovaleric acid derivatives) 9,17.
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页码：41 / 47
页数：7
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