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A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene

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dc.contributor.authorBon, David J.-Y. D
dc.contributor.authorBanwell, Martin
dc.contributor.authorWillis, Anthony
dc.date.accessioned2015-12-10T22:40:32Z
dc.date.issued2010
dc.date.updated2016-02-24T10:23:32Z
dc.description.abstractThe first total synthesis of the hirsutene-type sesquiterpenoid natural product (+)-connatusin B (2) is reported. The cis-1,2-dihydrocatechol 3, which is obtained in enantiomerically pure form via the enzymatic dihydroxylation of toluene, served as the starting material. Diels-Alder cycloaddition and oxa-di-π-methane rearrangement reactions represent key chemical steps in the reaction sequence leading to the cyclopropane ring-fused linear triquinane 14. Reductive cleavage of the three-membered ring within this framework and various functional group interconversions then provide the title compound 2.
dc.identifier.issn0040-4020
dc.identifier.urihttp://hdl.handle.net/1885/57495
dc.publisherElsevier
dc.sourceTetrahedron
dc.subjectKeywords: connatusin b; hirsutene; sesquiterpene derivative; unclassified drug; article; chemical reaction; cycloaddition; Diels Alder reaction; dihydroxylation; drug structure; drug synthesis; enantiomer; priority journal; Alnus Chemoenzymatic; Connatusin B; Diels-Alder; Oxa-di-p-methane; Photochemistry; Sesquiterpene
dc.titleA chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene
dc.typeJournal article
local.bibliographicCitation.issue39
local.bibliographicCitation.lastpage7814
local.bibliographicCitation.startpage7807
local.contributor.affiliationBon, David J.-Y. D, 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.contributor.authoruidBon, David J.-Y. D, u4490355
local.contributor.authoruidBanwell, Martin, u9500594
local.contributor.authoruidWillis, Anthony, u8512028
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
local.identifier.ariespublicationu4005981xPUB403
local.identifier.citationvolume66
local.identifier.doi10.1016/j.tet.2010.07.059
local.identifier.scopusID2-s2.0-77956392533
local.identifier.thomsonID000282071100016
local.type.statusPublished Version

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