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dc.contributor.authorReichl, Kyle D.en_US
dc.contributor.authorSmith, Michael J.en_US
dc.contributor.authorSong, Min K.en_US
dc.contributor.authorJohnson, Richard P.en_US
dc.contributor.authorPorco, John A.en_US
dc.date.accessioned2018-11-06T16:13:15Z
dc.date.available2018-11-06T16:13:15Z
dc.date.issued2017-10-11
dc.identifierhttp://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000413057100023&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=6e74115fe3da270499c3d65c9b17d654
dc.identifier.citationKyle D Reichl, Michael J Smith, Min K Song, Richard P Johnson, John A Porco. 2017. "Biomimetic Total Synthesis of (+/-)-Griffipavixanthone via a Cationic Cycloaddition-Cyclization Cascade." Journal Of The American Chemical Society, Volume 139, Issue 40, pp. 14053 - 14056 (4). https://doi.org/10.1021/jacs.7b09265
dc.identifier.issn0002-7863
dc.identifier.urihttps://hdl.handle.net/2144/31952
dc.descriptionPublished in final edited form as: J Am Chem Soc. 2017. October 11; 139(40): 14053–14056. doi:10.1021/jacs.7b09265.en_US
dc.description.abstractWe report the concise, biomimetic total synthesis of the dimeric, Diels-Alder natural product griffipavixanthone from a readily accessible prenylated xanthone monomer. The key step utilizes a novel intermolecular [4+2] cycloaddition-cyclization cascade between a vinyl p-quinone methide and an in situ generated isomeric diene promoted by either Lewis or Brønsted acids. Experimental and computational studies of the reaction pathway suggest that a stepwise, cationic Diels-Alder cycloaddition is operative.en_US
dc.description.sponsorshipWe thank the National Institutes of Health (NIH) (R35 GM-118173) and Boston University (BU) for financial support. K.D.R. is supported by a postdoctoral fellowship (PF-16-235-01-CDD) from the American Cancer Society. We thank Dr. Jeffrey Bacon (BU) for X-ray crystal structure analysis. NMR (CHE-0619339) and MS (CHE-0443618) facilities at BU are supported by the National Science Foundation (NSF). We thank Dr. Chao Qi and Ms. Kalina Doytchinova for helpful discussions. Work at the BU-CMD is supported by the NIH (R24 GM-111625). Research at UNH was supported by the NSF (CHE-1362519). This work used the Extreme Science and Engineering Discovery Environment (XSEDE), which is supported by the NSF under grant no. ACI-1548562. (R35 GM-118173 - National Institutes of Health (NIH); Boston University (BU); PF-16-235-01-CDD - American Cancer Society; National Science Foundation (NSF); R24 GM-111625 - NIH; CHE-1362519 - NSF; ACI-1548562 - NSF)en_US
dc.format.extentp. 14053 - 14056en_US
dc.languageEnglish
dc.publisherAmerican Chemical Societyen_US
dc.relation.ispartofJournal Of The American Chemical Society
dc.subjectScience & technologyen_US
dc.subjectPhysical sciencesen_US
dc.subjectChemistryen_US
dc.subjectPara-quinone methidesen_US
dc.subjectDiels-Alder reactionsen_US
dc.subjectGarcinia-oblongifoliaen_US
dc.subjectAllyl cationsen_US
dc.subjectIn-vitroen_US
dc.subjectXanthonesen_US
dc.subjectGriffipavixanthoneen_US
dc.subjectMechanismen_US
dc.subjectBarken_US
dc.subjectXanthochymusen_US
dc.subjectBiological productsen_US
dc.subjectBiomimeticsen_US
dc.subjectCrystallography, X-rayen_US
dc.subjectCyclizationen_US
dc.subjectCycloaddition reactionen_US
dc.subjectModels, molecularen_US
dc.subjectStereoisomerismen_US
dc.subjectXanthonesen_US
dc.subjectChemical sciencesen_US
dc.titleBiomimetic total synthesis of (+/-)-griffipavixanthone via a cationic cycloaddition-cyclization cascadeen_US
dc.typeArticleen_US
dc.description.versionAccepted manuscripten_US
dc.identifier.doi10.1021/jacs.7b09265
dc.identifier.pmid28942643
pubs.elements-sourceweb-of-scienceen_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


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