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: Kaufman, Teodoro Saúl, Bracca, Andrea Beatriz Juana, Larghi, Enrique Leandro, Pergomet, Jorgelina Leonor
Formato: article artículo publishedVersion
Lenguaje:Inglés
Publicado: Royal Society of Chemistry 2017
Materias:
Total synthesis
natural product
heterocycles
Verbesina luetzelburgii
benzofuranone
Acceso en línea:http://hdl.handle.net/2133/9261
http://hdl.handle.net/2133/9261
Aporte de:
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario
id I15-R121-2133-9261
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
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AT larghienriqueleandro firsttotalsynthesisoftheonlyknown2isopropyliden2hbenzofuran3oneisolatedfromvluetzelburgii
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bdutipo_str Repositorios
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