A Redox-Relay Heck Approach to Substituted Tetrahydrofurans

[Image: see text] An operationally simple and efficient strategy for the synthesis of substituted tetrahydrofurans from readily available cis-butene-1,4-diol is described. A redox-relay Heck reaction is used to rapidly access cyclic hemiacetals that can be directly reduced to afford the correspondin...

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Autores principales: Byrne, Tom J. M., Mylrea, Megan E., Cuthbertson, James D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10088021/
https://www.ncbi.nlm.nih.gov/pubmed/36988968
http://dx.doi.org/10.1021/acs.orglett.3c00769
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author Byrne, Tom J. M.
Mylrea, Megan E.
Cuthbertson, James D.
author_facet Byrne, Tom J. M.
Mylrea, Megan E.
Cuthbertson, James D.
author_sort Byrne, Tom J. M.
collection PubMed
description [Image: see text] An operationally simple and efficient strategy for the synthesis of substituted tetrahydrofurans from readily available cis-butene-1,4-diol is described. A redox-relay Heck reaction is used to rapidly access cyclic hemiacetals that can be directly reduced to afford the corresponding 3-aryl tetrahydrofuran. Furthermore, the hemiacetals can also serve as precursors to a range of disubstituted tetrahydrofurans, including the calyxolane natural products.
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spelling pubmed-100880212023-04-12 A Redox-Relay Heck Approach to Substituted Tetrahydrofurans Byrne, Tom J. M. Mylrea, Megan E. Cuthbertson, James D. Org Lett [Image: see text] An operationally simple and efficient strategy for the synthesis of substituted tetrahydrofurans from readily available cis-butene-1,4-diol is described. A redox-relay Heck reaction is used to rapidly access cyclic hemiacetals that can be directly reduced to afford the corresponding 3-aryl tetrahydrofuran. Furthermore, the hemiacetals can also serve as precursors to a range of disubstituted tetrahydrofurans, including the calyxolane natural products. American Chemical Society 2023-03-29 /pmc/articles/PMC10088021/ /pubmed/36988968 http://dx.doi.org/10.1021/acs.orglett.3c00769 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 Byrne, Tom J. M.
Mylrea, Megan E.
Cuthbertson, James D.
A Redox-Relay Heck Approach to Substituted Tetrahydrofurans
title A Redox-Relay Heck Approach to Substituted Tetrahydrofurans
title_full A Redox-Relay Heck Approach to Substituted Tetrahydrofurans
title_fullStr A Redox-Relay Heck Approach to Substituted Tetrahydrofurans
title_full_unstemmed A Redox-Relay Heck Approach to Substituted Tetrahydrofurans
title_short A Redox-Relay Heck Approach to Substituted Tetrahydrofurans
title_sort redox-relay heck approach to substituted tetrahydrofurans
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10088021/
https://www.ncbi.nlm.nih.gov/pubmed/36988968
http://dx.doi.org/10.1021/acs.orglett.3c00769
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