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Experimental and computational studies into an ATPH-promoted exo -Selective IMDA reaction: A short total synthesis of Δ 9 -THC

Pearson, Emma; Kanizaj, Nicholas; Willis, Anthony; Paddon-Row, Michael; Sherburn, Michael

Description

(Figure Presented) Reversal of fortune: The inherent cis stereoselectivity of an intramolecular Diels-Alder reaction is reversed through promotion with aluminum tris(2,6-diphenylphenoxide) (ATPH), allowing a total synthesis of the natural product Δ 9-tet

dc.contributor.authorPearson, Emma
dc.contributor.authorKanizaj, Nicholas
dc.contributor.authorWillis, Anthony
dc.contributor.authorPaddon-Row, Michael
dc.contributor.authorSherburn, Michael
dc.date.accessioned2015-12-10T22:40:23Z
dc.identifier.issn0947-6539
dc.identifier.urihttp://hdl.handle.net/1885/57445
dc.description.abstract(Figure Presented) Reversal of fortune: The inherent cis stereoselectivity of an intramolecular Diels-Alder reaction is reversed through promotion with aluminum tris(2,6-diphenylphenoxide) (ATPH), allowing a total synthesis of the natural product Δ 9-tet
dc.publisherWiley-VCH Verlag GMBH
dc.sourceChemistry, A European Journal
dc.subjectKeywords: Cannabinoids; Density-functional calculations; Diastereo-selectivity; Diels-Alder reaction; Total synthesis; Stereoselectivity; Synthesis (chemical); Cycloaddition; aluminum tris(2,6 diphenylphenoxide); aluminum tris(2,6-diphenylphenoxide); cannabinoid; c Cannabinoids; Density functional calculations; Diastereoselectivity; Diels-alder reactions; Total synthesis
dc.titleExperimental and computational studies into an ATPH-promoted exo -Selective IMDA reaction: A short total synthesis of Δ 9 -THC
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume16
dc.date.issued2010
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB401
local.type.statusPublished Version
local.contributor.affiliationPearson, Emma, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationKanizaj, Nicholas, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationPaddon-Row, Michael, University of New South Wales
local.contributor.affiliationSherburn, Michael, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue28
local.bibliographicCitation.startpage8280
local.bibliographicCitation.lastpage8284
local.identifier.doi10.1002/chem.201001176
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2016-02-24T10:23:32Z
local.identifier.scopusID2-s2.0-77954837403
local.identifier.thomsonID000280819100009
CollectionsANU Research Publications

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