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Factors controlling the biomimetic triple cyclisation of xylulose β-keto-esters to syringolides. Part 1: Synthesis of 4-deoxysyringolide 2.

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dc.contributor.authorBennett, Simon
dc.contributor.authorRickards, Rodney
dc.date.accessioned2015-12-13T23:12:04Z
dc.date.available2015-12-13T23:12:04Z
dc.date.issued2003
dc.date.updated2015-12-12T08:30:17Z
dc.description.abstractTreatment of the 4-deoxy-D-xylulose β-ketodecanoate 13c with basic alumina affords 4′-deoxysyringolide 2 14 as a single stereoisomer, indicating that the course of the biomimetic triple cyclisation of the corresponding D-xylulose ester 3b to syringolid
dc.identifier.issn0040-4039
dc.identifier.urihttp://hdl.handle.net/1885/87879
dc.publisherElsevier
dc.sourceTetrahedron Letters
dc.subjectKeywords: amide; syringolide; unclassified drug; xylulose; article; biomimetics; Knoevenagel condensation; Michael addition; stereoisomerism; synthesis 4'-deoxysyringolide 2; 4,5,6,7-tetranorsyringolide 1; Biomimetic; Cyclisation; Elicitor; Syringolide 2; Syringolide analogues; Xylulose ß-keto-esters
dc.titleFactors controlling the biomimetic triple cyclisation of xylulose β-keto-esters to syringolides. Part 1: Synthesis of 4-deoxysyringolide 2.
dc.typeJournal article
local.bibliographicCitation.issue36
local.bibliographicCitation.lastpage6930
local.bibliographicCitation.startpage6927
local.contributor.affiliationBennett, Simon, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationRickards, Rodney, College of Physical and Mathematical Sciences, ANU
local.contributor.authoruidBennett, Simon, u3447772
local.contributor.authoruidRickards, Rodney, v000238
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationMigratedxPub17352
local.identifier.citationvolume44
local.identifier.doi10.1016/S0040-4039(03)01682-4
local.identifier.scopusID2-s2.0-0042659716
local.type.statusPublished Version

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