Studies toward Providencin: The Furanyl-Cyclobutanol Segment

[Image: see text] The furanocembranoid providencin remains an unconquered bastion, although the synthesis of 17-deoxyprovidencin—lacking a single −OH group—has been accomplished in the past. This paper describes a practical approach to a properly hydroxylated building block via an iridium-catalyzed...

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Autores principales: Spohr, Simon M., Fürstner, Alois
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10012265/
https://www.ncbi.nlm.nih.gov/pubmed/36847332
http://dx.doi.org/10.1021/acs.orglett.3c00327
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author Spohr, Simon M.
Fürstner, Alois
author_facet Spohr, Simon M.
Fürstner, Alois
author_sort Spohr, Simon M.
collection PubMed
description [Image: see text] The furanocembranoid providencin remains an unconquered bastion, although the synthesis of 17-deoxyprovidencin—lacking a single −OH group—has been accomplished in the past. This paper describes a practical approach to a properly hydroxylated building block via an iridium-catalyzed photosensitized intramolecular [2 + 2] cycloaddition as the key step. While an attempt to convert this compound into providencin via RCAM failed, it might well be elaborated into the natural product by adopting the literature route.
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spelling pubmed-100122652023-03-15 Studies toward Providencin: The Furanyl-Cyclobutanol Segment Spohr, Simon M. Fürstner, Alois Org Lett [Image: see text] The furanocembranoid providencin remains an unconquered bastion, although the synthesis of 17-deoxyprovidencin—lacking a single −OH group—has been accomplished in the past. This paper describes a practical approach to a properly hydroxylated building block via an iridium-catalyzed photosensitized intramolecular [2 + 2] cycloaddition as the key step. While an attempt to convert this compound into providencin via RCAM failed, it might well be elaborated into the natural product by adopting the literature route. American Chemical Society 2023-02-27 /pmc/articles/PMC10012265/ /pubmed/36847332 http://dx.doi.org/10.1021/acs.orglett.3c00327 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 Spohr, Simon M.
Fürstner, Alois
Studies toward Providencin: The Furanyl-Cyclobutanol Segment
title Studies toward Providencin: The Furanyl-Cyclobutanol Segment
title_full Studies toward Providencin: The Furanyl-Cyclobutanol Segment
title_fullStr Studies toward Providencin: The Furanyl-Cyclobutanol Segment
title_full_unstemmed Studies toward Providencin: The Furanyl-Cyclobutanol Segment
title_short Studies toward Providencin: The Furanyl-Cyclobutanol Segment
title_sort studies toward providencin: the furanyl-cyclobutanol segment
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10012265/
https://www.ncbi.nlm.nih.gov/pubmed/36847332
http://dx.doi.org/10.1021/acs.orglett.3c00327
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