One-Pot Sequence of Staudinger/aza-Wittig/Castagnoli–Cushman Reactions Provides Facile Access to Novel Natural-like Polycyclic Ring Systems

Realization of the one-pot Staudinger/aza-Wittig/Castagnoli–Cushman reaction sequence for a series of azido aldehydes and homophthalic anhydrides is described. The reaction proceeded at room temperature and delivered novel polyheterocycles related to the natural product realm in high yields and high...

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Autores principales: Lebedev, Rodion, Dar’in, Dmitry, Kantin, Grigory, Bakulina, Olga, Krasavin, Mikhail
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9735558/
https://www.ncbi.nlm.nih.gov/pubmed/36500222
http://dx.doi.org/10.3390/molecules27238130
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author Lebedev, Rodion
Dar’in, Dmitry
Kantin, Grigory
Bakulina, Olga
Krasavin, Mikhail
author_facet Lebedev, Rodion
Dar’in, Dmitry
Kantin, Grigory
Bakulina, Olga
Krasavin, Mikhail
author_sort Lebedev, Rodion
collection PubMed
description Realization of the one-pot Staudinger/aza-Wittig/Castagnoli–Cushman reaction sequence for a series of azido aldehydes and homophthalic anhydrides is described. The reaction proceeded at room temperature and delivered novel polyheterocycles related to the natural product realm in high yields and high diastereoselectivity. The methodology has been extended to three other cyclic anhydrides. These further unravel the potential of the Castagnoli–Cushman reaction in generating polyheterocyclic molecular scaffolds.
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spelling pubmed-97355582022-12-11 One-Pot Sequence of Staudinger/aza-Wittig/Castagnoli–Cushman Reactions Provides Facile Access to Novel Natural-like Polycyclic Ring Systems Lebedev, Rodion Dar’in, Dmitry Kantin, Grigory Bakulina, Olga Krasavin, Mikhail Molecules Article Realization of the one-pot Staudinger/aza-Wittig/Castagnoli–Cushman reaction sequence for a series of azido aldehydes and homophthalic anhydrides is described. The reaction proceeded at room temperature and delivered novel polyheterocycles related to the natural product realm in high yields and high diastereoselectivity. The methodology has been extended to three other cyclic anhydrides. These further unravel the potential of the Castagnoli–Cushman reaction in generating polyheterocyclic molecular scaffolds. MDPI 2022-11-22 /pmc/articles/PMC9735558/ /pubmed/36500222 http://dx.doi.org/10.3390/molecules27238130 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Lebedev, Rodion
Dar’in, Dmitry
Kantin, Grigory
Bakulina, Olga
Krasavin, Mikhail
One-Pot Sequence of Staudinger/aza-Wittig/Castagnoli–Cushman Reactions Provides Facile Access to Novel Natural-like Polycyclic Ring Systems
title One-Pot Sequence of Staudinger/aza-Wittig/Castagnoli–Cushman Reactions Provides Facile Access to Novel Natural-like Polycyclic Ring Systems
title_full One-Pot Sequence of Staudinger/aza-Wittig/Castagnoli–Cushman Reactions Provides Facile Access to Novel Natural-like Polycyclic Ring Systems
title_fullStr One-Pot Sequence of Staudinger/aza-Wittig/Castagnoli–Cushman Reactions Provides Facile Access to Novel Natural-like Polycyclic Ring Systems
title_full_unstemmed One-Pot Sequence of Staudinger/aza-Wittig/Castagnoli–Cushman Reactions Provides Facile Access to Novel Natural-like Polycyclic Ring Systems
title_short One-Pot Sequence of Staudinger/aza-Wittig/Castagnoli–Cushman Reactions Provides Facile Access to Novel Natural-like Polycyclic Ring Systems
title_sort one-pot sequence of staudinger/aza-wittig/castagnoli–cushman reactions provides facile access to novel natural-like polycyclic ring systems
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9735558/
https://www.ncbi.nlm.nih.gov/pubmed/36500222
http://dx.doi.org/10.3390/molecules27238130
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