Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes

[Image: see text] Five-membered ring systems are ubiquitous throughout natural products and synthetic therapeutics, and thus, efficient methods to access this essential scaffold are required. Herein, we report the thioacid-mediated, 5-exo-trig cyclization of various 1,6-dienes, with high yields of u...

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Autores principales: Lynch, Dylan M., Nolan, Mark D., Williams, Conor, Van Dalsen, Leendert, Calvert, Susannah H., Dénès, Fabrice, Trujillo, Cristina, Scanlan, Eoin M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10367065/
https://www.ncbi.nlm.nih.gov/pubmed/37418624
http://dx.doi.org/10.1021/acs.joc.3c00824
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author Lynch, Dylan M.
Nolan, Mark D.
Williams, Conor
Van Dalsen, Leendert
Calvert, Susannah H.
Dénès, Fabrice
Trujillo, Cristina
Scanlan, Eoin M.
author_facet Lynch, Dylan M.
Nolan, Mark D.
Williams, Conor
Van Dalsen, Leendert
Calvert, Susannah H.
Dénès, Fabrice
Trujillo, Cristina
Scanlan, Eoin M.
author_sort Lynch, Dylan M.
collection PubMed
description [Image: see text] Five-membered ring systems are ubiquitous throughout natural products and synthetic therapeutics, and thus, efficient methods to access this essential scaffold are required. Herein, we report the thioacid-mediated, 5-exo-trig cyclization of various 1,6-dienes, with high yields of up to 98%. The labile thioester functionality can be exploited to generate a free thiol residue which can be used as a functional handle or removed entirely to provide the traceless cyclized product.
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spelling pubmed-103670652023-07-26 Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes Lynch, Dylan M. Nolan, Mark D. Williams, Conor Van Dalsen, Leendert Calvert, Susannah H. Dénès, Fabrice Trujillo, Cristina Scanlan, Eoin M. J Org Chem [Image: see text] Five-membered ring systems are ubiquitous throughout natural products and synthetic therapeutics, and thus, efficient methods to access this essential scaffold are required. Herein, we report the thioacid-mediated, 5-exo-trig cyclization of various 1,6-dienes, with high yields of up to 98%. The labile thioester functionality can be exploited to generate a free thiol residue which can be used as a functional handle or removed entirely to provide the traceless cyclized product. American Chemical Society 2023-07-07 /pmc/articles/PMC10367065/ /pubmed/37418624 http://dx.doi.org/10.1021/acs.joc.3c00824 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 Lynch, Dylan M.
Nolan, Mark D.
Williams, Conor
Van Dalsen, Leendert
Calvert, Susannah H.
Dénès, Fabrice
Trujillo, Cristina
Scanlan, Eoin M.
Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes
title Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes
title_full Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes
title_fullStr Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes
title_full_unstemmed Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes
title_short Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes
title_sort traceless thioacid-mediated radical cyclization of 1,6-dienes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10367065/
https://www.ncbi.nlm.nih.gov/pubmed/37418624
http://dx.doi.org/10.1021/acs.joc.3c00824
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