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dc.contributor.authorPurgett, Thomas J.en_US
dc.contributor.authorDyer, Matthew W.en_US
dc.contributor.authorBickel, Bryceen_US
dc.contributor.authorMcNeely, Jamesen_US
dc.contributor.authorPorco, John A.en_US
dc.coverage.spatialUnited Statesen_US
dc.date.accessioned2020-10-15T18:20:21Z
dc.date.available2020-10-15T18:20:21Z
dc.date.issued2019-09-25
dc.identifierhttps://www.ncbi.nlm.nih.gov/pubmed/31469554
dc.identifier.citationThomas J Purgett, Matthew W Dyer, Bryce Bickel, James McNeely, John A Porco. 2019. "Gold(I)-Mediated Cycloisomerization/Cycloaddition Enables Bioinspired Syntheses of Neonectrolides B-E and Analogues.." J Am Chem Soc, Volume 141, Issue 38, pp. 15135 - 15144. https://doi.org/10.1021/jacs.9b06355
dc.identifier.issn1520-5126
dc.identifier.urihttps://hdl.handle.net/2144/41466
dc.descriptionThe publisher's final edited version of this article is available at J Am Chem Soc. doi: 10.1021/jacs.9b06355en_US
dc.description.abstractDevelopment of a synthetic route to the oxaphenalenone (OP) natural products neonectrolides B-E is described. The synthesis relies on gold-catalyzed 6-endo-dig hydroarylation of an unusual enynol substrate as well as a one-pot Rieche formylation/cyclization/deprotection sequence to efficiently construct the tricyclic oxaphenalenone framework in the form of a masked ortho-quinone methide (o-QM). A tandem cycloisomerization/[4 + 2] cycloaddition strategy was employed to quickly construct molecules resembling the neonectrolides. The tricyclic OP natural product SF226 could be converted to corymbiferan lactone E and a related masked o-QM. Our study culminates with the application of the tandem reaction sequence to syntheses of neonectrolides B-E as well as previously unreported exo-diastereomers.en_US
dc.description.sponsorshipR35 GM118173 - NIGMS NIH HHSen_US
dc.format.extentp. 15135 - 15144en_US
dc.languageeng
dc.relation.ispartofJ Am Chem Soc
dc.subjectGeneral chemistryen_US
dc.subjectChemical sciencesen_US
dc.subjectOxaphenalenoneen_US
dc.subject[4+2] cycloadditionen_US
dc.subjectGold catalysisen_US
dc.subjectOrtho-quinone methideen_US
dc.titleGold(I)-mediated cycloisomerization/cycloaddition enables bioinspired syntheses of neonectrolides B-E and analoguesen_US
dc.typeArticleen_US
dc.description.versionAccepted manuscripten_US
dc.identifier.doi10.1021/jacs.9b06355
dc.identifier.pmid31469554
pubs.elements-sourcepubmeden_US
pubs.notesEmbargo: Not knownen_US
pubs.organisational-groupBoston Universityen_US
pubs.organisational-groupBoston University, College of Arts & Sciencesen_US
pubs.organisational-groupBoston University, College of Arts & Sciences, Department of Chemistryen_US
pubs.publication-statusPublisheden_US
dc.identifier.mycv487864


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