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Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework

Tang, Fei; Lan, Ping; Bolte, Benoit; Banwell, Martin; Ward, James; Willis, Anthony

Description

A total synthesis of the title sesquiterpene 4 is described that starts with the chiral, non-racemic cis-1,2-dihydrocatechol 10 obtained through the whole-cell biotransformation of p-iodotoluene. Compound 10 is elaborated over seven steps, including Negishi cross-coupling and intramolecular Diels–Alder (IMDA) cycloaddition reactions, to ketone 7 that engages in a photochemically promoted 1,3-acyl migration and so affording cyclobutanone 6. Compound 6 was converted over further steps into the...[Show more]

dc.contributor.authorTang, Fei
dc.contributor.authorLan, Ping
dc.contributor.authorBolte, Benoit
dc.contributor.authorBanwell, Martin
dc.contributor.authorWard, James
dc.contributor.authorWillis, Anthony
dc.date.accessioned2020-02-10T01:20:48Z
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/201573
dc.description.abstractA total synthesis of the title sesquiterpene 4 is described that starts with the chiral, non-racemic cis-1,2-dihydrocatechol 10 obtained through the whole-cell biotransformation of p-iodotoluene. Compound 10 is elaborated over seven steps, including Negishi cross-coupling and intramolecular Diels–Alder (IMDA) cycloaddition reactions, to ketone 7 that engages in a photochemically promoted 1,3-acyl migration and so affording cyclobutanone 6. Compound 6 was converted over further steps into the title compound 4.
dc.description.sponsorshipWe thank the Australian Research Council and the Institute of Advanced Studies for financial support. F.T. and P.L. are the grateful recipients of funding provided by the CSC of the Government of the People’s Republic of China.
dc.format.extent8 pages
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherAmerican Chemical Society
dc.rights© 2018 American Chemical Society
dc.sourceJournal of Organic Chemistry
dc.titleTotal Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume83
dc.date.issued2018-10-25
local.identifier.absfor039904 - Organometallic Chemistry
local.identifier.absfor030207 - Transition Metal Chemistry
local.identifier.absfor030204 - Main Group Metal Chemistry
local.identifier.ariespublicationu3102795xPUB1388
local.publisher.urlhttps://pubs.acs.org/
local.type.statusPublished Version
local.contributor.affiliationTang, Fei, College of Science, The Australian National University
local.contributor.affiliationLan, Ping, College of Science, The Australian National University
local.contributor.affiliationBolte, Benoit, College of Science, The Australian National University
local.contributor.affiliationBanwell, Martin, College of Science, The Australian National University
local.contributor.affiliationWard, James, College of Science, The Australian National University
local.contributor.affiliationWillis, Anthony, College of Science, The Australian National University
local.description.embargo2037-12-31
local.identifier.essn1520-6904
local.bibliographicCitation.issue22
local.bibliographicCitation.startpage14049
local.bibliographicCitation.lastpage14056
local.identifier.doi10.1021/acs.joc.8b02626
local.identifier.absseo970102 - Expanding Knowledge in the Physical Sciences
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2019-11-25T07:30:36Z
local.identifier.scopusID2-s2.0-85056555739
CollectionsANU Research Publications

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