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Chemoenzymatic Methods for the Enantioselective Preparation of Sesquiterpenoid Natural Products from Aromatic Precursors

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Banwell, Martin; Edwards, Alison; Harfoot, Gwion; Jolliffe, Katrina; McLeod, Malcolm; McRae, Kenneth; Stewart, Scott; Vogtle, Markus

Description

The enantiomerically pure cis-1,2-dihydrocatechols 2, which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain examples of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (-)-patchoulenone and (-)-hirsutene.

dc.contributor.authorBanwell, Martin
dc.contributor.authorEdwards, Alison
dc.contributor.authorHarfoot, Gwion
dc.contributor.authorJolliffe, Katrina
dc.contributor.authorMcLeod, Malcolm
dc.contributor.authorMcRae, Kenneth
dc.contributor.authorStewart, Scott
dc.contributor.authorVogtle, Markus
dc.date.accessioned2015-12-13T23:06:01Z
dc.identifier.issn0033-4545
dc.identifier.urihttp://hdl.handle.net/1885/85830
dc.description.abstractThe enantiomerically pure cis-1,2-dihydrocatechols 2, which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain examples of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (-)-patchoulenone and (-)-hirsutene.
dc.publisherInternational Union of Pure and Applied Chemistry
dc.sourcePure and Applied Chemistry
dc.subjectKeywords: alkene derivative; catechol derivative; hirsutene; sesquiterpenoid; conference paper; cycloaddition; Diels Alder reaction; dihydroxylation; enantiomer; priority journal; stereochemistry; synthesis; technique
dc.titleChemoenzymatic Methods for the Enantioselective Preparation of Sesquiterpenoid Natural Products from Aromatic Precursors
dc.typeJournal article
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.citationvolume75
dc.date.issued2003
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationMigratedxPub14494
local.type.statusPublished Version
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationEdwards, Alison, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationHarfoot, Gwion, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationJolliffe, Katrina, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationMcLeod, Malcolm, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationMcRae, Kenneth, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationStewart, Scott, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationVogtle, Markus, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue2-3
local.bibliographicCitation.startpage223
local.bibliographicCitation.lastpage229
dc.date.updated2015-12-12T08:03:24Z
local.identifier.scopusID2-s2.0-0037318016
CollectionsANU Research Publications

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