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| Campo DC | Valor | Lengua/Idioma |
|---|---|---|
| dc.provenance | Universidad Nacional de Rosario.RepHipUNR | - |
| dc.creator | Kaufman, Teodoro Saúl | - |
| dc.creator | Bracca, Andrea Beatriz Juana | - |
| dc.creator | Larghi, Enrique Leandro | - |
| dc.creator | Pergomet, Jorgelina Leonor | - |
| dc.date | 2017-01-17 | - |
| dc.date | 2017-01-17 | - |
| dc.date.accessioned | 2019-07-15T19:02:36Z | - |
| dc.date.available | 2019-07-15T19:02:36Z | - |
| dc.date.issued | 2017-01-17 | - |
| dc.date.issued | 2017-01-17 | - |
| dc.identifier | 1759-9679 | - |
| dc.identifier | http://hdl.handle.net/2133/9261 | - |
| dc.identifier | 10.1039/C6RA28587B | - |
| dc.identifier | http://hdl.handle.net/2133/9261 | - |
| dc.identifier.uri | http://rodna.bn.gov.ar/jspui/handle/bnmm/570502 | - |
| dc.description | The 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. | - |
| dc.description | Fil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. | - |
| dc.description | Fil: Bracca, Andrea Beatriz Juana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. | - |
| dc.description | Fil: Larghi, Enrique Leandro. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. | - |
| dc.description | Fil: Pergomet, Jorgelina Leonor. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. | - |
| dc.format | application/pdf | - |
| dc.language | eng | - |
| dc.publisher | Royal Society of Chemistry | - |
| dc.rights | info:eu-repo/semantics/openAccess | - |
| dc.source | reponame:RepHipUNR (UNR) | - |
| dc.source | instname:Universidad Nacional de Rosario | - |
| dc.source | instacron:UNR | - |
| dc.source.uri | http://hdl.handle.net/2133/9261 | - |
| dc.subject | Total synthesis | - |
| dc.subject | natural product | - |
| dc.subject | heterocycles | - |
| dc.subject | Verbesina luetzelburgii | - |
| dc.subject | benzofuranone | - |
| dc.title | First total synthesis of the only known 2- isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii | - |
| dc.type | info:eu-repo/semantics/article | - |
| dc.type | info:eu-repo/semantics/publishedVersion | - |
| dc.type | artículo | - |
| dc.type | info:ar-repo/semantics/articulo | - |
| Aparece en las colecciones: | Universidad Nacional de Rosario. RepHipUNR | |
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