A biomimetic approach for the concise total synthesis of greenwaylactams A–C

A concise, racemic total synthesis of three sesquiterpenoid alkaloids (greenwaylactams A–C) exhibiting an unprecedented 8-membered benzolactam is disclosed. Key transformations of this work include the ring expansion through cleavage of an indole via Witkop oxidation, as well as an HFIP mediated cat...

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Detalles Bibliográficos
Autores principales: Kratena, Nicolas, Weil, Matthias, Gärtner, Peter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10410498/
https://www.ncbi.nlm.nih.gov/pubmed/37496493
http://dx.doi.org/10.1039/d3ob01001e
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author Kratena, Nicolas
Weil, Matthias
Gärtner, Peter
author_facet Kratena, Nicolas
Weil, Matthias
Gärtner, Peter
author_sort Kratena, Nicolas
collection PubMed
description A concise, racemic total synthesis of three sesquiterpenoid alkaloids (greenwaylactams A–C) exhibiting an unprecedented 8-membered benzolactam is disclosed. Key transformations of this work include the ring expansion through cleavage of an indole via Witkop oxidation, as well as an HFIP mediated cationic cyclisation to build up the pentacyclic carbon skeleton.
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spelling pubmed-104104982023-08-10 A biomimetic approach for the concise total synthesis of greenwaylactams A–C Kratena, Nicolas Weil, Matthias Gärtner, Peter Org Biomol Chem Chemistry A concise, racemic total synthesis of three sesquiterpenoid alkaloids (greenwaylactams A–C) exhibiting an unprecedented 8-membered benzolactam is disclosed. Key transformations of this work include the ring expansion through cleavage of an indole via Witkop oxidation, as well as an HFIP mediated cationic cyclisation to build up the pentacyclic carbon skeleton. The Royal Society of Chemistry 2023-07-24 /pmc/articles/PMC10410498/ /pubmed/37496493 http://dx.doi.org/10.1039/d3ob01001e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Kratena, Nicolas
Weil, Matthias
Gärtner, Peter
A biomimetic approach for the concise total synthesis of greenwaylactams A–C
title A biomimetic approach for the concise total synthesis of greenwaylactams A–C
title_full A biomimetic approach for the concise total synthesis of greenwaylactams A–C
title_fullStr A biomimetic approach for the concise total synthesis of greenwaylactams A–C
title_full_unstemmed A biomimetic approach for the concise total synthesis of greenwaylactams A–C
title_short A biomimetic approach for the concise total synthesis of greenwaylactams A–C
title_sort biomimetic approach for the concise total synthesis of greenwaylactams a–c
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10410498/
https://www.ncbi.nlm.nih.gov/pubmed/37496493
http://dx.doi.org/10.1039/d3ob01001e
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