Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity

A 15-step chemoenzymatic total synthesis of C-1 methoxycarbonyl narciclasine (10) was accomplished. The synthesis began with the toluene dioxygenase-mediated dihydroxylation of ortho-dibromobenzene to provide the corresponding cis-dihydrodiol (12) as a single enantiomer. Further key steps included a...

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Autores principales: Habaz, Lihi, Bedard, Korey, Smith, Mitchell, Du, Liqin, Kornienko, Alexander, Hudlicky, Tomas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9230822/
https://www.ncbi.nlm.nih.gov/pubmed/35744934
http://dx.doi.org/10.3390/molecules27123809
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author Habaz, Lihi
Bedard, Korey
Smith, Mitchell
Du, Liqin
Kornienko, Alexander
Hudlicky, Tomas
author_facet Habaz, Lihi
Bedard, Korey
Smith, Mitchell
Du, Liqin
Kornienko, Alexander
Hudlicky, Tomas
author_sort Habaz, Lihi
collection PubMed
description A 15-step chemoenzymatic total synthesis of C-1 methoxycarbonyl narciclasine (10) was accomplished. The synthesis began with the toluene dioxygenase-mediated dihydroxylation of ortho-dibromobenzene to provide the corresponding cis-dihydrodiol (12) as a single enantiomer. Further key steps included a nitroso Diels–Alder reaction and an intramolecular Heck cyclization. The C-1 homolog 10 was tested and evaluated for antiproliferative activity against natural narciclasine (1) as the positive control. Experimental and spectral data are reported for all novel compounds.
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spelling pubmed-92308222022-06-25 Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity Habaz, Lihi Bedard, Korey Smith, Mitchell Du, Liqin Kornienko, Alexander Hudlicky, Tomas Molecules Article A 15-step chemoenzymatic total synthesis of C-1 methoxycarbonyl narciclasine (10) was accomplished. The synthesis began with the toluene dioxygenase-mediated dihydroxylation of ortho-dibromobenzene to provide the corresponding cis-dihydrodiol (12) as a single enantiomer. Further key steps included a nitroso Diels–Alder reaction and an intramolecular Heck cyclization. The C-1 homolog 10 was tested and evaluated for antiproliferative activity against natural narciclasine (1) as the positive control. Experimental and spectral data are reported for all novel compounds. MDPI 2022-06-14 /pmc/articles/PMC9230822/ /pubmed/35744934 http://dx.doi.org/10.3390/molecules27123809 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Habaz, Lihi
Bedard, Korey
Smith, Mitchell
Du, Liqin
Kornienko, Alexander
Hudlicky, Tomas
Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity
title Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity
title_full Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity
title_fullStr Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity
title_full_unstemmed Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity
title_short Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity
title_sort design and synthesis of c-1 methoxycarbonyl derivative of narciclasine and its biological activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9230822/
https://www.ncbi.nlm.nih.gov/pubmed/35744934
http://dx.doi.org/10.3390/molecules27123809
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