Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions

[Image: see text] Aromatic hydroxylation reactions catalyzed by heme-thiolate enzymes proceed via an epoxide intermediate. These aromatic epoxides could be valuable building blocks for organic synthesis giving access to a range of chiral trans-disubstituted cyclohexadiene synthons. Here, we show tha...

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Autores principales: Zhang, Wuyuan, Li, Huanhuan, Younes, Sabry H. H., Gómez de Santos, Patricia, Tieves, Florian, Grogan, Gideon, Pabst, Martin, Alcalde, Miguel, Whitwood, Adrian C., Hollmann, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7976598/
https://www.ncbi.nlm.nih.gov/pubmed/33763289
http://dx.doi.org/10.1021/acscatal.0c05588
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author Zhang, Wuyuan
Li, Huanhuan
Younes, Sabry H. H.
Gómez de Santos, Patricia
Tieves, Florian
Grogan, Gideon
Pabst, Martin
Alcalde, Miguel
Whitwood, Adrian C.
Hollmann, Frank
author_facet Zhang, Wuyuan
Li, Huanhuan
Younes, Sabry H. H.
Gómez de Santos, Patricia
Tieves, Florian
Grogan, Gideon
Pabst, Martin
Alcalde, Miguel
Whitwood, Adrian C.
Hollmann, Frank
author_sort Zhang, Wuyuan
collection PubMed
description [Image: see text] Aromatic hydroxylation reactions catalyzed by heme-thiolate enzymes proceed via an epoxide intermediate. These aromatic epoxides could be valuable building blocks for organic synthesis giving access to a range of chiral trans-disubstituted cyclohexadiene synthons. Here, we show that naphthalene epoxides generated by fungal peroxygenases can be subjected to nucleophilic ring opening, yielding non-racemic trans-disubstituted cyclohexadiene derivates, which in turn can be used for further chemical transformations. This approach may represent a promising shortcut for the synthesis of natural products and APIs.
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spelling pubmed-79765982021-03-22 Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions Zhang, Wuyuan Li, Huanhuan Younes, Sabry H. H. Gómez de Santos, Patricia Tieves, Florian Grogan, Gideon Pabst, Martin Alcalde, Miguel Whitwood, Adrian C. Hollmann, Frank ACS Catal [Image: see text] Aromatic hydroxylation reactions catalyzed by heme-thiolate enzymes proceed via an epoxide intermediate. These aromatic epoxides could be valuable building blocks for organic synthesis giving access to a range of chiral trans-disubstituted cyclohexadiene synthons. Here, we show that naphthalene epoxides generated by fungal peroxygenases can be subjected to nucleophilic ring opening, yielding non-racemic trans-disubstituted cyclohexadiene derivates, which in turn can be used for further chemical transformations. This approach may represent a promising shortcut for the synthesis of natural products and APIs. American Chemical Society 2021-02-12 2021-03-05 /pmc/articles/PMC7976598/ /pubmed/33763289 http://dx.doi.org/10.1021/acscatal.0c05588 Text en © 2021 The Authors. Published by American Chemical Society This is an open access article published under an ACS AuthorChoice License (https://creativecommons.org/licenses/by-nc-nd/4.0/) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Zhang, Wuyuan
Li, Huanhuan
Younes, Sabry H. H.
Gómez de Santos, Patricia
Tieves, Florian
Grogan, Gideon
Pabst, Martin
Alcalde, Miguel
Whitwood, Adrian C.
Hollmann, Frank
Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions
title Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions
title_full Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions
title_fullStr Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions
title_full_unstemmed Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions
title_short Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions
title_sort biocatalytic aromaticity-breaking epoxidation of naphthalene and nucleophilic ring-opening reactions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7976598/
https://www.ncbi.nlm.nih.gov/pubmed/33763289
http://dx.doi.org/10.1021/acscatal.0c05588
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