Petasis Sequence Reactions for the Scaffold-Diverse Synthesis of Bioactive Polycyclic Small Molecules

[Image: see text] The multicomponent Petasis reaction is a versatile method to access functionalized amines. The combination of Petasis reaction with subsequent ring-closing reactions is a powerful strategy to build novel polycyclic scaffolds. In this study, we report the generation of a diverse set...

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Autores principales: Avathan Veettil, Amrutha K., Kirchhoff, Jan-Lukas, Brieger, Lukas, Strohmann, Carsten, Wu, Peng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9835185/
https://www.ncbi.nlm.nih.gov/pubmed/36643548
http://dx.doi.org/10.1021/acsomega.2c06585
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author Avathan Veettil, Amrutha K.
Kirchhoff, Jan-Lukas
Brieger, Lukas
Strohmann, Carsten
Wu, Peng
author_facet Avathan Veettil, Amrutha K.
Kirchhoff, Jan-Lukas
Brieger, Lukas
Strohmann, Carsten
Wu, Peng
author_sort Avathan Veettil, Amrutha K.
collection PubMed
description [Image: see text] The multicomponent Petasis reaction is a versatile method to access functionalized amines. The combination of Petasis reaction with subsequent ring-closing reactions is a powerful strategy to build novel polycyclic scaffolds. In this study, we report the generation of a diverse set of small molecules with polycyclic scaffolds featuring a high content of sp(3)-hybridized carbon atoms and multiple stereogenic centers by employing three-component Petasis reaction (3C-PR)—Intramolecular Diels–Alder (IMDA) and 3C-PR—ring-closing metathesis (RCM)—IMDA sequence reactions. This work demonstrates the wide substrate tolerance and broad applicability to access unexplored polycyclic scaffolds of biological interest using Petasis sequence reactions.
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spelling pubmed-98351852023-01-13 Petasis Sequence Reactions for the Scaffold-Diverse Synthesis of Bioactive Polycyclic Small Molecules Avathan Veettil, Amrutha K. Kirchhoff, Jan-Lukas Brieger, Lukas Strohmann, Carsten Wu, Peng ACS Omega [Image: see text] The multicomponent Petasis reaction is a versatile method to access functionalized amines. The combination of Petasis reaction with subsequent ring-closing reactions is a powerful strategy to build novel polycyclic scaffolds. In this study, we report the generation of a diverse set of small molecules with polycyclic scaffolds featuring a high content of sp(3)-hybridized carbon atoms and multiple stereogenic centers by employing three-component Petasis reaction (3C-PR)—Intramolecular Diels–Alder (IMDA) and 3C-PR—ring-closing metathesis (RCM)—IMDA sequence reactions. This work demonstrates the wide substrate tolerance and broad applicability to access unexplored polycyclic scaffolds of biological interest using Petasis sequence reactions. American Chemical Society 2022-12-16 /pmc/articles/PMC9835185/ /pubmed/36643548 http://dx.doi.org/10.1021/acsomega.2c06585 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Avathan Veettil, Amrutha K.
Kirchhoff, Jan-Lukas
Brieger, Lukas
Strohmann, Carsten
Wu, Peng
Petasis Sequence Reactions for the Scaffold-Diverse Synthesis of Bioactive Polycyclic Small Molecules
title Petasis Sequence Reactions for the Scaffold-Diverse Synthesis of Bioactive Polycyclic Small Molecules
title_full Petasis Sequence Reactions for the Scaffold-Diverse Synthesis of Bioactive Polycyclic Small Molecules
title_fullStr Petasis Sequence Reactions for the Scaffold-Diverse Synthesis of Bioactive Polycyclic Small Molecules
title_full_unstemmed Petasis Sequence Reactions for the Scaffold-Diverse Synthesis of Bioactive Polycyclic Small Molecules
title_short Petasis Sequence Reactions for the Scaffold-Diverse Synthesis of Bioactive Polycyclic Small Molecules
title_sort petasis sequence reactions for the scaffold-diverse synthesis of bioactive polycyclic small molecules
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9835185/
https://www.ncbi.nlm.nih.gov/pubmed/36643548
http://dx.doi.org/10.1021/acsomega.2c06585
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