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Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks

Jackson, Kerrie; Elsworth, Jon; Banwell, Martin; Willis, Anthony

Description

New and simple protocols are described for the conversion of the enzymatically-derived and enantiomerically pure cis-1,2-dihydrocatechol 7 (X = I) and its 6-methylated derivative into either antipodal form of compounds embodying the tricyclic frameworks of terpenoids 1-6. Key steps include intramolecular Diels-Alder (IMDA) and (in some cases) singlet or triplet-based photochemical processes.

dc.contributor.authorJackson, Kerrie
dc.contributor.authorElsworth, Jon
dc.contributor.authorBanwell, Martin
dc.contributor.authorWillis, Anthony
dc.date.accessioned2015-12-10T22:35:06Z
dc.identifier.issn1477-0520
dc.identifier.urihttp://hdl.handle.net/1885/56130
dc.description.abstractNew and simple protocols are described for the conversion of the enzymatically-derived and enantiomerically pure cis-1,2-dihydrocatechol 7 (X = I) and its 6-methylated derivative into either antipodal form of compounds embodying the tricyclic frameworks of terpenoids 1-6. Key steps include intramolecular Diels-Alder (IMDA) and (in some cases) singlet or triplet-based photochemical processes.
dc.publisherRoyal Society of Chemistry
dc.sourceOrganic and Biomolecular Chemistry
dc.subjectKeywords: Diels-Alder; Photochemical process; SIMPLE protocol; Terpenoids; bicyclo compound; octane; terpene; tricyclic antidepressant agent; article; catalysis; chemical model; chemical structure; chemistry; cyclization; enzyme activation; stereoisomerism; synthes
dc.titleChemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume8
dc.date.issued2010
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB352
local.type.statusPublished Version
local.contributor.affiliationJackson, Kerrie, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationElsworth, Jon, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue4
local.bibliographicCitation.startpage751
local.bibliographicCitation.lastpage754
local.identifier.doi10.1039/b921600f
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2016-02-24T10:23:21Z
local.identifier.scopusID2-s2.0-76249108432
local.identifier.thomsonID000274262200003
CollectionsANU Research Publications

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