Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B

dc.creatorSimonetti, Sebastián Osvaldo
dc.creatorLarghi, Enrique Leandro
dc.creatorBracca, Andrea Beatriz Juana
dc.creatorKaufman, Teodoro Saul
dc.date.accessioned2020-06-23T21:17:20Z
dc.date.accessioned2022-10-15T07:37:47Z
dc.date.available2020-06-23T21:17:20Z
dc.date.available2022-10-15T07:37:47Z
dc.date.created2020-06-23T21:17:20Z
dc.date.issued2012-03
dc.identifierSimonetti, Sebastián Osvaldo; Larghi, Enrique Leandro; Bracca, Andrea Beatriz Juana; Kaufman, Teodoro Saul; Synthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 10; 3-2012; 4124-4134
dc.identifier1477-0520
dc.identifierhttp://hdl.handle.net/11336/108052
dc.identifier1477-0539
dc.identifierCONICET Digital
dc.identifierCONICET
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/4361243
dc.description.abstractThe synthesis of the tricyclic angular chromone structure originally assigned to aspergillitine is reported. The synthesis was achieved in 11 steps and 15% overall yield from 2,4-dihydroxypropiophenone, through the intermediacy of 2,3-dimethyl-7-hydroxychromen-4-one. Construction of the nitrogen-bearing heterocyclic ring entailed a Stille cross-coupling reaction with n-Bu3SnCH2CHCH2, followed by double bond isomerization, oximation of the chromone carbonyl, and a final microwave-assisted electrocyclization of the thus formed 6π-electron aza-triene system.
dc.languageeng
dc.publisherRoyal Society of Chemistry
dc.relationinfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2012/OB/c2ob25067e#!divAbstract
dc.relationinfo:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/c2ob25067e
dc.rightshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.rightsinfo:eu-repo/semantics/restrictedAccess
dc.rightsAtribución-NoComercial-CompartirIgual 2.5 Argentina (CC BY-NC-SA 2.5 AR)
dc.subjectASPERGILLITINE
dc.subjectNATURAL PRODUCTS SYNTHESES
dc.subjectTMC-120B
dc.subject6-PI-ELECTROCYCLIZATION
dc.titleSynthesis of the unique angular tricyclic chromone structure proposed for aspergillitine, and its relationship with alkaloid TMC-120B
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:ar-repo/semantics/artículo
dc.typeinfo:eu-repo/semantics/publishedVersion


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