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N-Fmoc-dehydroalanine: a versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids

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Burkett, Brenden; Chai, Christina

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The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed. (C) 2000 Elsevier Science Ltd.

dc.contributor.authorBurkett, Brenden
dc.contributor.authorChai, Christina
dc.date.accessioned2015-12-13T23:22:01Z
dc.identifier.issn0040-4039
dc.identifier.urihttp://hdl.handle.net/1885/91242
dc.description.abstractThe synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed. (C) 2000 Elsevier Science Ltd.
dc.publisherElsevier
dc.sourceTetrahedron Letters
dc.subjectKeywords: alpha amino acid; cysteine; dehydroalanine; polymer; article; chemical reaction; chemical structure; oxidation; proton nuclear magnetic resonance; reaction analysis; synthesis Dehydroalanine; Diels-Alder reactions; Solid-phase synthesis
dc.titleN-Fmoc-dehydroalanine: a versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids
dc.typeJournal article
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.citationvolume41
dc.date.issued2000
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationMigratedxPub21924
local.type.statusPublished Version
local.contributor.affiliationBurkett, Brenden, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationChai, Christina, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.startpage6661
local.bibliographicCitation.lastpage6664
local.identifier.doi10.1016/S0040-4039(00)01113-8
dc.date.updated2015-12-12T09:09:34Z
local.identifier.scopusID2-s2.0-0034686852
CollectionsANU Research Publications

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