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First total synthesis of the only known 2- isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii

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dc.citation.titleRSC Advances
dc.citation.volume7
dc.creatorKaufman, Teodoro Saúl
dc.creatorBracca, Andrea Beatriz Juana
dc.creatorLarghi, Enrique Leandro
dc.creatorPergomet, Jorgelina Leonor
dc.date.accessioned2017-11-09T14:14:29Z
dc.date.available2017-11-09T14:14:29Z
dc.date.issued2017-01-17
dc.descriptionThe first total synthesis of 5-(1-hydroxy-1-ethyl)-2-isopropyliden-2H-benzofuran-3-one, is reported in its racemic and in one of its optically active [(S)-( )] forms. This heterocycle, isolated from Verbesina luetzelburgii, is the only known 2-isopropyliden-2H-benzofuran-3-one produced by species of Verbesina. The sequence took place in eight steps and 19% overall yield (up to 33% for the chiral form), from 40-hydroxyacetophenone. It entailed carbonyl group protection as the 1,3-dioxolane and a phenol ortho formylation, followed by a Williamson etherification with chloroacetone and an organocatalytic cross-aldolization, to afford a 2-acetyl-2,3-dihydrobenzofuran-3-ol intermediate. The latter underwent a methyl Grignard addition to the carbonyl moiety, followed by selective oxidation of the benzylic alcohol and deprotection, resulting in a b-hydroxy diketone derivative. A MsCl-assisted dehydration of the tertiary alcohol, established the isopropylidene motif, whereas the syntheses culminated by chemical or enzymatic (carrot, celeriac) selective reductions of the exocyclic carbonyl group.es
dc.description.filFil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina.
dc.description.filFil: Bracca, Andrea Beatriz Juana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina.
dc.description.filFil: Larghi, Enrique Leandro. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina.
dc.description.filFil: Pergomet, Jorgelina Leonor. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina.
dc.formatapplication/pdf
dc.identifier.doi10.1039/C6RA28587B
dc.identifier.issn1759-9679
dc.identifier.urihttp://hdl.handle.net/2133/9261
dc.language.isoenges
dc.publisherRoyal Society of Chemistryes
dc.rightsopenAccesses
dc.rights.urihttps://creativecommons.org/licenses/by-nc/3.0/*
dc.subjectTotal synthesises
dc.subjectnatural productes
dc.subjectheterocycleses
dc.subjectVerbesina luetzelburgiies
dc.subjectbenzofuranonees
dc.titleFirst total synthesis of the only known 2- isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgiies
dc.typearticle
dc.typeartículo
dc.typepublishedVersion

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