First total synthesis of the only known 2- isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii
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...
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Autores principales: | , , , |
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Formato: | article artículo publishedVersion |
Lenguaje: | Inglés |
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Royal Society of Chemistry
2017
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Materias: | |
Acceso en línea: | http://hdl.handle.net/2133/9261 http://hdl.handle.net/2133/9261 |
Aporte de: |
id |
I15-R121-2133-9261 |
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record_format |
dspace |
institution |
Universidad Nacional de Rosario |
institution_str |
I-15 |
repository_str |
R-121 |
collection |
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) |
language |
Inglés |
orig_language_str_mv |
eng |
topic |
Total synthesis natural product heterocycles Verbesina luetzelburgii benzofuranone |
spellingShingle |
Total synthesis natural product heterocycles Verbesina luetzelburgii benzofuranone Kaufman, Teodoro Saúl Bracca, Andrea Beatriz Juana Larghi, Enrique Leandro Pergomet, Jorgelina Leonor First total synthesis of the only known 2- isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii |
topic_facet |
Total synthesis natural product heterocycles Verbesina luetzelburgii benzofuranone |
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. |
format |
article artículo publishedVersion |
author |
Kaufman, Teodoro Saúl Bracca, Andrea Beatriz Juana Larghi, Enrique Leandro Pergomet, Jorgelina Leonor |
author_facet |
Kaufman, Teodoro Saúl Bracca, Andrea Beatriz Juana Larghi, Enrique Leandro Pergomet, Jorgelina Leonor |
author_sort |
Kaufman, Teodoro Saúl |
title |
First total synthesis of the only known 2- isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii |
title_short |
First total synthesis of the only known 2- isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii |
title_full |
First total synthesis of the only known 2- isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii |
title_fullStr |
First total synthesis of the only known 2- isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii |
title_full_unstemmed |
First total synthesis of the only known 2- isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii |
title_sort |
first total synthesis of the only known 2- isopropyliden-2h-benzofuran-3-one isolated from v. luetzelburgii |
publisher |
Royal Society of Chemistry |
publishDate |
2017 |
url |
http://hdl.handle.net/2133/9261 http://hdl.handle.net/2133/9261 |
work_keys_str_mv |
AT kaufmanteodorosaul firsttotalsynthesisoftheonlyknown2isopropyliden2hbenzofuran3oneisolatedfromvluetzelburgii AT braccaandreabeatrizjuana firsttotalsynthesisoftheonlyknown2isopropyliden2hbenzofuran3oneisolatedfromvluetzelburgii AT larghienriqueleandro firsttotalsynthesisoftheonlyknown2isopropyliden2hbenzofuran3oneisolatedfromvluetzelburgii AT pergometjorgelinaleonor firsttotalsynthesisoftheonlyknown2isopropyliden2hbenzofuran3oneisolatedfromvluetzelburgii |
bdutipo_str |
Repositorios |
_version_ |
1764820413812047877 |