Chemoselective Ring Closure of 4-(3-Methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal Leading to Pandalizine A

[Image: see text] Starting from methylmaleic anhydride, a facile total synthesis of pandalizine A alkaloid is described via the regioselective reduction of methylmaleimide and acid-catalyzed enolization of 4-(3-methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal followed by chemoselective intramolecular...

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Autores principales: Yadav, Mahesh B., Pandhade, Kailas R., Argade, Narshinha P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6964528/
https://www.ncbi.nlm.nih.gov/pubmed/31956837
http://dx.doi.org/10.1021/acsomega.9b03760
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author Yadav, Mahesh B.
Pandhade, Kailas R.
Argade, Narshinha P.
author_facet Yadav, Mahesh B.
Pandhade, Kailas R.
Argade, Narshinha P.
author_sort Yadav, Mahesh B.
collection PubMed
description [Image: see text] Starting from methylmaleic anhydride, a facile total synthesis of pandalizine A alkaloid is described via the regioselective reduction of methylmaleimide and acid-catalyzed enolization of 4-(3-methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal followed by chemoselective intramolecular dehydrative cyclization as the key steps. It is noteworthy that the analogous model system with an additional β-methyl group followed an alternative chemoselective intermolecular aldol condensation pathway.
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spelling pubmed-69645282020-01-17 Chemoselective Ring Closure of 4-(3-Methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal Leading to Pandalizine A Yadav, Mahesh B. Pandhade, Kailas R. Argade, Narshinha P. ACS Omega [Image: see text] Starting from methylmaleic anhydride, a facile total synthesis of pandalizine A alkaloid is described via the regioselective reduction of methylmaleimide and acid-catalyzed enolization of 4-(3-methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal followed by chemoselective intramolecular dehydrative cyclization as the key steps. It is noteworthy that the analogous model system with an additional β-methyl group followed an alternative chemoselective intermolecular aldol condensation pathway. American Chemical Society 2019-12-26 /pmc/articles/PMC6964528/ /pubmed/31956837 http://dx.doi.org/10.1021/acsomega.9b03760 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Yadav, Mahesh B.
Pandhade, Kailas R.
Argade, Narshinha P.
Chemoselective Ring Closure of 4-(3-Methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal Leading to Pandalizine A
title Chemoselective Ring Closure of 4-(3-Methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal Leading to Pandalizine A
title_full Chemoselective Ring Closure of 4-(3-Methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal Leading to Pandalizine A
title_fullStr Chemoselective Ring Closure of 4-(3-Methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal Leading to Pandalizine A
title_full_unstemmed Chemoselective Ring Closure of 4-(3-Methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal Leading to Pandalizine A
title_short Chemoselective Ring Closure of 4-(3-Methyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)butanal Leading to Pandalizine A
title_sort chemoselective ring closure of 4-(3-methyl-2-oxo-2,5-dihydro-1h-pyrrol-1-yl)butanal leading to pandalizine a
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6964528/
https://www.ncbi.nlm.nih.gov/pubmed/31956837
http://dx.doi.org/10.1021/acsomega.9b03760
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AT argadenarshinhap chemoselectiveringclosureof43methyl2oxo25dihydro1hpyrrol1ylbutanalleadingtopandalizinea

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