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Oxetane Synthesis via Alcohol C–H Functionalization
[Image: see text] Oxetanes are strained heterocycles with unique properties that have triggered significant advances in medicinal chemistry. However, their synthesis still presents significant challenges that limit the use of this class of compounds in practical applications. In this Letter, we pres...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10375527/ https://www.ncbi.nlm.nih.gov/pubmed/37462721 http://dx.doi.org/10.1021/jacs.3c04891 |
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author | Paul, Subhasis Filippini, Dario Ficarra, Filippo Melnychenko, Heorhii Janot, Christopher Silvi, Mattia |
author_facet | Paul, Subhasis Filippini, Dario Ficarra, Filippo Melnychenko, Heorhii Janot, Christopher Silvi, Mattia |
author_sort | Paul, Subhasis |
collection | PubMed |
description | [Image: see text] Oxetanes are strained heterocycles with unique properties that have triggered significant advances in medicinal chemistry. However, their synthesis still presents significant challenges that limit the use of this class of compounds in practical applications. In this Letter, we present a methodology that introduces a new synthetic disconnection to access oxetanes from native alcohol substrates. The generality of the approach is demonstrated by the application in late-stage functionalization chemistry, which is further exploited to develop a single-step synthesis of a known bioactive synthetic steroid derivative that previously required at least four synthetic steps from available precursors. |
format | Online Article Text |
id | pubmed-10375527 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-103755272023-07-29 Oxetane Synthesis via Alcohol C–H Functionalization Paul, Subhasis Filippini, Dario Ficarra, Filippo Melnychenko, Heorhii Janot, Christopher Silvi, Mattia J Am Chem Soc [Image: see text] Oxetanes are strained heterocycles with unique properties that have triggered significant advances in medicinal chemistry. However, their synthesis still presents significant challenges that limit the use of this class of compounds in practical applications. In this Letter, we present a methodology that introduces a new synthetic disconnection to access oxetanes from native alcohol substrates. The generality of the approach is demonstrated by the application in late-stage functionalization chemistry, which is further exploited to develop a single-step synthesis of a known bioactive synthetic steroid derivative that previously required at least four synthetic steps from available precursors. American Chemical Society 2023-07-18 /pmc/articles/PMC10375527/ /pubmed/37462721 http://dx.doi.org/10.1021/jacs.3c04891 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 | Paul, Subhasis Filippini, Dario Ficarra, Filippo Melnychenko, Heorhii Janot, Christopher Silvi, Mattia Oxetane Synthesis via Alcohol C–H Functionalization |
title | Oxetane Synthesis via
Alcohol C–H Functionalization |
title_full | Oxetane Synthesis via
Alcohol C–H Functionalization |
title_fullStr | Oxetane Synthesis via
Alcohol C–H Functionalization |
title_full_unstemmed | Oxetane Synthesis via
Alcohol C–H Functionalization |
title_short | Oxetane Synthesis via
Alcohol C–H Functionalization |
title_sort | oxetane synthesis via
alcohol c–h functionalization |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10375527/ https://www.ncbi.nlm.nih.gov/pubmed/37462721 http://dx.doi.org/10.1021/jacs.3c04891 |
work_keys_str_mv | AT paulsubhasis oxetanesynthesisviaalcoholchfunctionalization AT filippinidario oxetanesynthesisviaalcoholchfunctionalization AT ficarrafilippo oxetanesynthesisviaalcoholchfunctionalization AT melnychenkoheorhii oxetanesynthesisviaalcoholchfunctionalization AT janotchristopher oxetanesynthesisviaalcoholchfunctionalization AT silvimattia oxetanesynthesisviaalcoholchfunctionalization |