A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core

The bicyclic tetrahydro-1,2-oxazine subunit of gliovirin is synthesized through a diastereoselective copper-catalyzed cyclization of an N-hydroxyamino ester. Oxidative elaboration to the fully functionalized bicycle was achieved through a series of mild transformations. Central to this approach was...

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Detalles Bibliográficos
Autores principales: Cowper, Nicholas G. W., Hesse, Matthew J., Chan, Katie M., Reisman, Sarah E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162951/
https://www.ncbi.nlm.nih.gov/pubmed/34094417
http://dx.doi.org/10.1039/d0sc04802j
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author Cowper, Nicholas G. W.
Hesse, Matthew J.
Chan, Katie M.
Reisman, Sarah E.
author_facet Cowper, Nicholas G. W.
Hesse, Matthew J.
Chan, Katie M.
Reisman, Sarah E.
author_sort Cowper, Nicholas G. W.
collection PubMed
description The bicyclic tetrahydro-1,2-oxazine subunit of gliovirin is synthesized through a diastereoselective copper-catalyzed cyclization of an N-hydroxyamino ester. Oxidative elaboration to the fully functionalized bicycle was achieved through a series of mild transformations. Central to this approach was the development of the first catalytic, enantioselective propargylation of an oxime to furnish a key N-hydroyxamino ester intermediate.
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spelling pubmed-81629512021-06-04 A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core Cowper, Nicholas G. W. Hesse, Matthew J. Chan, Katie M. Reisman, Sarah E. Chem Sci Chemistry The bicyclic tetrahydro-1,2-oxazine subunit of gliovirin is synthesized through a diastereoselective copper-catalyzed cyclization of an N-hydroxyamino ester. Oxidative elaboration to the fully functionalized bicycle was achieved through a series of mild transformations. Central to this approach was the development of the first catalytic, enantioselective propargylation of an oxime to furnish a key N-hydroyxamino ester intermediate. The Royal Society of Chemistry 2020-10-15 /pmc/articles/PMC8162951/ /pubmed/34094417 http://dx.doi.org/10.1039/d0sc04802j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Cowper, Nicholas G. W.
Hesse, Matthew J.
Chan, Katie M.
Reisman, Sarah E.
A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core
title A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core
title_full A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core
title_fullStr A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core
title_full_unstemmed A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core
title_short A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core
title_sort copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162951/
https://www.ncbi.nlm.nih.gov/pubmed/34094417
http://dx.doi.org/10.1039/d0sc04802j
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