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Synthesis of the himandrine skeleton

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dc.contributor.authorO'Connor, Patrick
dc.contributor.authorMander, Lewis
dc.contributor.authorMcLachlan, Matthew
dc.date.accessioned2015-12-13T22:41:18Z
dc.date.available2015-12-13T22:41:18Z
dc.date.issued2004
dc.date.updated2015-12-11T10:00:40Z
dc.description.abstractThe hexacyclic himandrine skeleton 5, which is present in the most complex alkaloids of the tropical rain forest tree Galbulimima belgraveana, has been prepared for the first time. The synthesis begins from the known [3.2.1]benzobicyclooctene intermediate 10. Key steps include a Diels-Alder cycloaddition, Curtius rearrangement, Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/1885/78442
dc.publisherAmerican Chemical Society
dc.sourceOrganic Letters
dc.subjectKeywords: alkaloid derivative; alkene derivative; himandrine; unclassified drug; amination; article; Birch reduction; chemical analysis; chemical modification; chemical structure; Curtius rearrangement; cycloaddition; Diels Alder reaction; Galbulimima belgraveana;
dc.titleSynthesis of the himandrine skeleton
dc.typeJournal article
local.bibliographicCitation.issue5
local.bibliographicCitation.lastpage706
local.bibliographicCitation.startpage703
local.contributor.affiliationO'Connor, Patrick, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationMander, Lewis, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationMcLachlan, Matthew, College of Physical and Mathematical Sciences, ANU
local.contributor.authoruidO'Connor, Patrick, u4023192
local.contributor.authoruidMander, Lewis, u7500768
local.contributor.authoruidMcLachlan, Matthew, u9617426
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationMigratedxPub7087
local.identifier.citationvolume6
local.identifier.doi10.1021/ol036308n
local.identifier.scopusID2-s2.0-1642328227
local.type.statusPublished Version

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