| dc.creator | Kaufman, Teodoro Saúl | |
| dc.creator | Bracca, Andrea Beatriz Juana | |
| dc.creator | Larghi, Enrique Leandro | |
| dc.creator | Pergomet, Jorgelina Leonor | |
| dc.date | 2017-11-09T14:14:29Z | |
| dc.date | 2017-11-09T14:14:29Z | |
| dc.date | 2017-01-17 | |
| dc.date | 2017-11-09T14:14:29Z | |
| dc.date | 2017-11-09T14:14:29Z | |
| dc.date | 2017-01-17 | |
| dc.date.accessioned | 2019-05-17T20:21:58Z | |
| dc.date.available | 2019-05-17T20:21:58Z | |
| 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://repositorioslatinoamericanos.uchile.cl/handle/2250/2679580 | |
| 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 | https://creativecommons.org/licenses/by-nc/3.0/ | |
| dc.rights | openAccess | |
| 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 | Artículos de revistas | |
| dc.type | Artículos de revistas | |
| dc.type | Artículos de revistas | |
