ACID-CATALYZED O-ALLYLATION OF BETA-HYDROXY-ALPHA-AMINO ACIDS - AN ENTRY INTO CONFORMATIONALLY CONSTRAINED DIPEPTIDE SURROGATES

被引：6

作者：

BURKHOLDER, TP

LE, TB

GIROUX, EL

FLYNN, GA

机构：

[1] Marion Merrell Dow Research Institute, Cincinnati, OH 45215

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1992年 / 2卷 / 06期

关键词：

D O I：

10.1016/S0960-894X(01)81201-4

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

O-Allylation using allyl trichloroimidate 5 was found to be an effective method for the introduction of an acetaldehyde equivalent onto the hydroxyl group of beta-hydroxy-alpha-amino acid derivatives. Rigid oxygen containing tricyclic anti-phenylalanyl-leucine mimic 1 was efficiently synthesized using this method. This mimetic was further elaborated to provide 7c, a potent inhibitor of angiotensin-1 converting enzyme (ACE).

引用

页码：579 / 582

页数：4

共 7 条

[1] ASYMMETRIC-SYNTHESIS OF ANTI-BETA-HYDROXY-ALPHA-AMINO ACIDS
EVANS, DA
SJOGREN, EB
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[2] AN ACYL-IMINIUM ION CYCLIZATION ROUTE TO A NOVEL CONFORMATIONALLY RESTRICTED DIPEPTIDE MIMIC - APPLICATIONS TO ANGIOTENSIN-CONVERTING ENZYME-INHIBITION
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[5] RENIN INHIBITORS - DESIGN AND SYNTHESIS OF A NEW CLASS OF CONFORMATIONALLY RESTRICTED ANALOGS OF ANGIOTENSINOGEN
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[6] A FAVORABLE DIASTEREOSELECTIVE SYNTHESIS OF N-(1-S-ETHOXYCARBONYL-3-PHENYLPROPYL)-S-ALANINE
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[J]. TETRAHEDRON LETTERS, 1984, 25 (11) : 1143 - 1146
[7] ACID-CATALYZED BENZYLATION AND ALLYLATION BY ALKYL TRICHLOROACETIMIDATES
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IVERSEN, T
BUNDLE, DR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2247 - 2250

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