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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Formato: | article artículo publishedVersion |
Lenguaje: | Inglés |
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Wiley
2018
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Materias: | |
Acceso en línea: | http://hdl.handle.net/2133/10498 http://hdl.handle.net/2133/10498 |
Aporte de: |
id |
I15-R121-2133-10498 |
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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 |
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 |
_version_ |
1764820408427610114 |