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The Pd-catalyzed Alder-ene reactions of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes as a new route to C3a-arylhexahydroindoles: towards the total synthesis of tazettine

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Lehmann, Anna; Willis, Anthony; Banwell, Martin

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A series of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes (4) has been prepared. Several of these have been shown to undergo an intramolecular Alder-ene reaction in the presence of palladium acetate and the ligand BBEDA to afford C3a-arylhexahydroindoles of the general form 1. Certain of these products may serve as precursors to the alkaloid tazettine (2).

dc.contributor.authorLehmann, Anna
dc.contributor.authorWillis, Anthony
dc.contributor.authorBanwell, Martin
dc.date.accessioned2015-12-10T22:41:24Z
dc.identifier.issn0004-9425
dc.identifier.urihttp://hdl.handle.net/1885/57883
dc.description.abstractA series of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes (4) has been prepared. Several of these have been shown to undergo an intramolecular Alder-ene reaction in the presence of palladium acetate and the ligand BBEDA to afford C3a-arylhexahydroindoles of the general form 1. Certain of these products may serve as precursors to the alkaloid tazettine (2).
dc.publisherCSIRO Publishing
dc.sourceAustralian Journal of Chemistry
dc.subjectKeywords: Alder-ene reaction; Cyclohexenes; Intramolecular alder-ene reaction; Palladium acetate; Total synthesis; Organometallics; Synthesis (chemical); Palladium
dc.titleThe Pd-catalyzed Alder-ene reactions of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes as a new route to C3a-arylhexahydroindoles: towards the total synthesis of tazettine
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume63
dc.date.issued2010
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB419
local.type.statusPublished Version
local.contributor.affiliationLehmann, Anna, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue12
local.bibliographicCitation.startpage1655
local.bibliographicCitation.lastpage1678
local.identifier.doi10.1071/CH10359
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2016-02-24T10:23:43Z
local.identifier.scopusID2-s2.0-78650114488
local.identifier.thomsonID000285007800011
CollectionsANU Research Publications

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