Expedient approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for the synthesis of TMC-120B, pseudodeflectusin, and Their congeners

A straightforward approach toward 6-bromo-2-isopropylidenecoumaranone, a potential intermediate toward alkaloid TMC 120-B, pseudodeflectusin, and other natural products, was reported. The synthetic sequence involved the reaction of 3-bromosalicylaldehyde with chloroacetone and cyclization of the r...

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Autores principales: Pergomet, Jorgelina Leonor, Kaufman, Teodoro Saúl, Bracca, Andrea Beatriz Juana
Formato: article artículo publishedVersion
Lenguaje:Inglés
Publicado: Wiley 2018
Materias:
6-Bromo-2-isopropylidenecoumaranone
TMC-120B
Pseudodeflectusin
Natural Product Synthesis
Prolinemediated Cyclization
Acceso en línea:http://hdl.handle.net/2133/10498
http://hdl.handle.net/2133/10498
Aporte de:
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario
id I15-R121-2133-10498
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 6-Bromo-2-isopropylidenecoumaranone
TMC-120B
Pseudodeflectusin
Natural Product Synthesis
Prolinemediated Cyclization
spellingShingle 6-Bromo-2-isopropylidenecoumaranone
TMC-120B
Pseudodeflectusin
Natural Product Synthesis
Prolinemediated Cyclization
Pergomet, Jorgelina Leonor
Kaufman, Teodoro Saúl
Bracca, Andrea Beatriz Juana
Expedient approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for the synthesis of TMC-120B, pseudodeflectusin, and Their congeners
topic_facet 6-Bromo-2-isopropylidenecoumaranone
TMC-120B
Pseudodeflectusin
Natural Product Synthesis
Prolinemediated Cyclization
description A straightforward approach toward 6-bromo-2-isopropylidenecoumaranone, a potential intermediate toward alkaloid TMC 120-B, pseudodeflectusin, and other natural products, was reported. The synthetic sequence involved the reaction of 3-bromosalicylaldehyde with chloroacetone and cyclization of the resulting ether to a 2-acetylcoumaranol intermediate. This was followed by sequential methyl Grignard addition and Jones’ oxidation to the corresponding coumaranone, which was dehydrated to the final product with the methanesulfonyl chloride/pyridine reagent. The protection of the coumaranol as the corresponding THP-ether resulted in improved product yields.
format article
artículo
publishedVersion
author Pergomet, Jorgelina Leonor
Kaufman, Teodoro Saúl
Bracca, Andrea Beatriz Juana
author_facet Pergomet, Jorgelina Leonor
Kaufman, Teodoro Saúl
Bracca, Andrea Beatriz Juana
author_sort Pergomet, Jorgelina Leonor
title Expedient approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for the synthesis of TMC-120B, pseudodeflectusin, and Their congeners
title_short Expedient approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for the synthesis of TMC-120B, pseudodeflectusin, and Their congeners
title_full Expedient approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for the synthesis of TMC-120B, pseudodeflectusin, and Their congeners
title_fullStr Expedient approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for the synthesis of TMC-120B, pseudodeflectusin, and Their congeners
title_full_unstemmed Expedient approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for the synthesis of TMC-120B, pseudodeflectusin, and Their congeners
title_sort expedient approach to 6-bromo-2-isopropylidenecoumaranone, a potential intermediate for the synthesis of tmc-120b, pseudodeflectusin, and their congeners
publisher Wiley
publishDate 2018
url http://hdl.handle.net/2133/10498
http://hdl.handle.net/2133/10498
work_keys_str_mv AT pergometjorgelinaleonor expedientapproachto6bromo2isopropylidenecoumaranoneapotentialintermediateforthesynthesisoftmc120bpseudodeflectusinandtheircongeners
AT kaufmanteodorosaul expedientapproachto6bromo2isopropylidenecoumaranoneapotentialintermediateforthesynthesisoftmc120bpseudodeflectusinandtheircongeners
AT braccaandreabeatrizjuana expedientapproachto6bromo2isopropylidenecoumaranoneapotentialintermediateforthesynthesisoftmc120bpseudodeflectusinandtheircongeners
bdutipo_str Repositorios
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