A flexible approach to the gamma-amino-beta-hydroxy acid moiety of hapalosin

A flexible approach to ethyl (3R,4S)-N-Boc-4-amino-3-hydroxy-5-phenylpentanoate (N-Boc-AHPPA-OEt), the gamma-amino-beta-hydroxy acid moiety of hapalosin is described. The synthetic method features a ring-opening ethanolysis of an activated N-Boc-lactam, which is obtained via a diastereoselective red...

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Bibliographic Details
Published inChinese journal of chemistry Vol. 21; no. 7; pp. 723 - 726
Main Authors Huang, PQ, Wu, TJ, Ye, JL
Format Journal Article
LanguageEnglish
Published BEIJING SCIENCE CHINA PRESS 01.07.2003
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
ANALOGS
EFFICIENT SYNTHESIS
RESISTANCE-REVERSING ACTIVITY
(S)-MALIC ACID
hapalosin
CYCLIC DEPSIPEPTIDE
anzi-AHPPA
AGENT HAPALOSIN
asymmetric synthesis
DIASTEREOSELECTIVE SYNTHESIS
CONFORMATIONAL-ANALYSIS
MULTIDRUG-RESISTANCE
reductive alkylation
(R)-malic acid
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Summary:A flexible approach to ethyl (3R,4S)-N-Boc-4-amino-3-hydroxy-5-phenylpentanoate (N-Boc-AHPPA-OEt), the gamma-amino-beta-hydroxy acid moiety of hapalosin is described. The synthetic method features a ring-opening ethanolysis of an activated N-Boc-lactam, which is obtained via a diastereoselective reductive-alkylation of (R)-malimide derivative. The flexibility of the method resides in the introduction of the alkyl side chain by B Grignard reagent addition.
ISSN:1001-604X
DOI:10.1002/cjoc.20030210704