Asymmetric synthesis of novel quaternary α-Hydroxy-δ-lactam dipeptide surrogates

Application of the Sharpless AD protocol to a series of α-( E)-benzylidene-δ-lactam precursors followed by selective deoxygenation provided efficient synthetic routes to the chiral quaternary α-hydroxy-γ-lactam derivatives 4 and 5. These functionalized intermediates and the diol precursors 3 are reg...

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Bibliographic Details
Published inBioorganic & medicinal chemistry letters Vol. 9; no. 17; pp. 2625 - 2628
Main Authors Minami, Nathaniel K., Reiner, John E., Semple, J. Edward
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 06.09.1999
Elsevier
Subjects
Chemistry
Dipeptides - chemical synthesis
Dipeptides - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Lactams - chemistry
Organic chemistry
Preparations and properties
Protein Structure, Quaternary
Hydroxylation
Nitrogen heterocycle
Lactam
Sharpless ligand
Chemical reduction
Organic thiocarbonate
Asymmetric synthesis
Tertiary alcohol
Six membered ring
Deoxygenation
Piperidine derivatives
Chemical synthesis
Glycol
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Summary:Application of the Sharpless AD protocol to a series of α-( E)-benzylidene-δ-lactam precursors followed by selective deoxygenation provided efficient synthetic routes to the chiral quaternary α-hydroxy-γ-lactam derivatives 4 and 5. These functionalized intermediates and the diol precursors 3 are regarded as novel types of D-Phe-Pro dipeptide surrogates that are useful as enzyme active site probes.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(99)00448-5