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Chemoenzymatic Total Syntheses of the Enantiomers of the Protoilludanes 8-Deoxydihydrotsugicoline and Radudiol

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Chang, Ee Ling; Bolte, Benoit; Lan, Ping; Willis, Anthony; Banwell, Martin

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Chemoenzymatic and stereoselective total syntheses of the non-natural enantiomeric forms of the recently isolated protoilludane natural products 8-deoxydihydrotsugicoline (1) and radudiol (2) (viz. ent-1 and ent-2, respectively) are reported. The key steps involve the Diels-Alder cycloaddition of cyclopent-2-en-1-one to the acetonide derived from enantiomerically pure and enzymatically derived cis-1,2-dihydrocatechol 3, elaboration of the resulting adduct to the tricyclic ketone 12, and a...[Show more]

dc.contributor.authorChang, Ee Ling
dc.contributor.authorBolte, Benoit
dc.contributor.authorLan, Ping
dc.contributor.authorWillis, Anthony
dc.contributor.authorBanwell, Martin
dc.date.accessioned2021-01-07T00:20:57Z
dc.date.available2021-01-07T00:20:57Z
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/219209
dc.description.abstractChemoenzymatic and stereoselective total syntheses of the non-natural enantiomeric forms of the recently isolated protoilludane natural products 8-deoxydihydrotsugicoline (1) and radudiol (2) (viz. ent-1 and ent-2, respectively) are reported. The key steps involve the Diels-Alder cycloaddition of cyclopent-2-en-1-one to the acetonide derived from enantiomerically pure and enzymatically derived cis-1,2-dihydrocatechol 3, elaboration of the resulting adduct to the tricyclic ketone 12, and a photochemically promoted rearrangement of this last compound to the octahydro-1H-cyclobuta[e]indenone 13.
dc.description.sponsorshipWe thank the Australian Research Council and the Institute of Advanced Studies for financial support. E.L.C. was the grateful recipient of an Australian Postgraduate Award provided by the Australian Government, and P.L. acknowledges receipt of a CSC Ph.D. Scholarship provided by the Government of the People’s Republic of China
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherAmerican Chemical Society
dc.rights© 2016 American Chemical Society
dc.sourceThe Journal of organic chemistry
dc.subjectbiological products
dc.subjectcatechols
dc.subjectcycloaddition reaction
dc.subjectindenes
dc.subjectmolecular structure
dc.subjectpolycyclic sesquiterpenes
dc.subjectsesquiterpenes
dc.subjectstereoisomerism
dc.titleChemoenzymatic Total Syntheses of the Enantiomers of the Protoilludanes 8-Deoxydihydrotsugicoline and Radudiol
dc.typeJournal article
local.identifier.citationvolume81
dc.date.issued2016-03-04
local.publisher.urlhttp://pubs.acs.org/journal/joceah/about.html
local.type.statusAccepted Version
local.contributor.affiliationChang, E. L., Research School of Chemistry, Institute of Advanced Studies, The Australian National University
local.contributor.affiliationBolte, B., Research School of Chemistry, Institute of Advanced Studies, The Australian National University
local.contributor.affiliationLan, P., Research School of Chemistry, Institute of Advanced Studies, The Australian National University
local.contributor.affiliationWillis, A., Research School of Chemistry, Institute of Advanced Studies, The Australian National University
local.contributor.affiliationBanwell, M., Research School of Chemistry, Institute of Advanced Studies, The Australian National University
dc.relationhttp://purl.org/au-research/grants/arc/DP150101947
local.identifier.essn1520-6904
local.bibliographicCitation.issue5
local.bibliographicCitation.startpage2078
local.bibliographicCitation.lastpage2086
local.identifier.doi10.1021/acs.joc.6b00043
dcterms.accessRightsOpen Access
dc.provenancehttps://v2.sherpa.ac.uk/id/publication/7797..."The Accepted Version can be archived in a Non-Commercial Institutional Repository If Required by Funder, If Required by Institution. 12 months embargo " from SHERPA/RoMEO site (as at 7/01/2021). This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/acs.joc.6b00043
CollectionsANU Research Publications

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