Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound

[Image: see text] Developing new procedures for the synthesis of tetrahydropyrans in a very stereoselective manner is of great importance for the synthesis of THP-containing natural products. Here, we report an interesting protocol for the synthesis of polysubstituted halogenated tetrahydropyrans by...

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Autores principales: Díez-Poza, Carlos, Fernández-Peña, Laura, González-Andrés, Paula, Barbero, Asunción
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10242753/
https://www.ncbi.nlm.nih.gov/pubmed/37220201
http://dx.doi.org/10.1021/acs.joc.3c00050
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author Díez-Poza, Carlos
Fernández-Peña, Laura
González-Andrés, Paula
Barbero, Asunción
author_facet Díez-Poza, Carlos
Fernández-Peña, Laura
González-Andrés, Paula
Barbero, Asunción
author_sort Díez-Poza, Carlos
collection PubMed
description [Image: see text] Developing new procedures for the synthesis of tetrahydropyrans in a very stereoselective manner is of great importance for the synthesis of THP-containing natural products. Here, we report an interesting protocol for the synthesis of polysubstituted halogenated tetrahydropyrans by silyl-Prins cyclization of vinylsilyl alcohols, in which the nature of the Lewis acid determines the outcome of the process. The methodology has been applied to the synthesis of a known antinociceptive.
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spelling pubmed-102427532023-06-07 Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound Díez-Poza, Carlos Fernández-Peña, Laura González-Andrés, Paula Barbero, Asunción J Org Chem [Image: see text] Developing new procedures for the synthesis of tetrahydropyrans in a very stereoselective manner is of great importance for the synthesis of THP-containing natural products. Here, we report an interesting protocol for the synthesis of polysubstituted halogenated tetrahydropyrans by silyl-Prins cyclization of vinylsilyl alcohols, in which the nature of the Lewis acid determines the outcome of the process. The methodology has been applied to the synthesis of a known antinociceptive. American Chemical Society 2023-05-23 /pmc/articles/PMC10242753/ /pubmed/37220201 http://dx.doi.org/10.1021/acs.joc.3c00050 Text en © 2023 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 Díez-Poza, Carlos
Fernández-Peña, Laura
González-Andrés, Paula
Barbero, Asunción
Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound
title Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound
title_full Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound
title_fullStr Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound
title_full_unstemmed Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound
title_short Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound
title_sort changing the reaction pathway of silyl-prins cyclization by switching the lewis acid: application to the synthesis of an antinociceptive compound
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10242753/
https://www.ncbi.nlm.nih.gov/pubmed/37220201
http://dx.doi.org/10.1021/acs.joc.3c00050
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