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Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria

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dc.contributor.authorMudianta, Wayan
dc.contributor.authorKatavic, Peter L
dc.contributor.authorLambert, Lynette K
dc.contributor.authorHayes, Patricia Y
dc.contributor.authorBanwell, Martin
dc.contributor.authorMunro, Murray HG
dc.contributor.authorBernhardt, Paul
dc.contributor.authorGarson, Mary J
dc.date.accessioned2015-12-07T22:30:48Z
dc.date.issued2010
dc.date.updated2016-02-24T09:51:27Z
dc.description.abstractChemical analysis of an Indonesian sponge sample has provided three new 3-alkylpiperidine alkaloids, tetradehydrohaliclonacyclamine A, its mono-N-oxide derivative, and a 2-epi isomer. The absolute structure of tetradehydrohaliclonacyclamine A has been established by X-ray crystallography from anomalous dispersion effects using Cu radiation, which determined that the absolute configuration is 2S, 3S, 7S, 9S while an HPLC study revealed that the alkaloid is enantiomerically pure.
dc.identifier.issn0040-4020
dc.identifier.urihttp://hdl.handle.net/1885/22474
dc.publisherElsevier
dc.sourceTetrahedron
dc.subjectKeywords: alkaloid derivative; alkyl group; copper; piperidine derivative; tetradehydrohaliclonacyclamine a; unclassified drug; article; drug structure; enantiomer; halichondria; high performance liquid chromatography; Indonesia; irradiation; isomer; nonhuman; nucl 3-Alkylpiperidine; Absolute configuration; Biosynthesis; Halichondria; N-Oxide; NMR; Sponge; X-ray analysis
dc.titleStructure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria
dc.typeJournal article
local.bibliographicCitation.issue14
local.bibliographicCitation.lastpage2760
local.bibliographicCitation.startpage2752
local.contributor.affiliationMudianta, Wayan, University of Queensland
local.contributor.affiliationKatavic, Peter L, University of Queensland
local.contributor.affiliationLambert, Lynette K, University of Queensland
local.contributor.affiliationHayes, Patricia Y, University of Queensland
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationMunro, Murray HG, University of Canterbury
local.contributor.affiliationBernhardt, Paul, University of Queensland
local.contributor.affiliationGarson, Mary J, University of Queensland
local.contributor.authoruidBanwell, Martin, u9500594
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030502 - Natural Products Chemistry
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
local.identifier.ariespublicationu2544221xPUB22
local.identifier.citationvolume66
local.identifier.doi10.1016/j.tet.2010.01.068
local.identifier.scopusID2-s2.0-77649190429
local.type.statusPublished Version

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