Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine

Bromination of the furanoquinoline alkaloid haplophyllidine by molecular bromine and N-bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The st...

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Autores principales: Ubaidullaev, A. U., Vinogradova, V. I., Zhurakulov, Sh. N., Mukarramov, N. I., Bobakulov, Kh. M., Turgunov, K. A., Tashkhodzhaev, B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer US 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9664044/
https://www.ncbi.nlm.nih.gov/pubmed/36406158
http://dx.doi.org/10.1007/s10600-022-03877-6
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author Ubaidullaev, A. U.
Vinogradova, V. I.
Zhurakulov, Sh. N.
Mukarramov, N. I.
Bobakulov, Kh. M.
Turgunov, K. A.
Tashkhodzhaev, B.
author_facet Ubaidullaev, A. U.
Vinogradova, V. I.
Zhurakulov, Sh. N.
Mukarramov, N. I.
Bobakulov, Kh. M.
Turgunov, K. A.
Tashkhodzhaev, B.
author_sort Ubaidullaev, A. U.
collection PubMed
description Bromination of the furanoquinoline alkaloid haplophyllidine by molecular bromine and N-bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The structures and absolute configurations of the chiral centers of all four bromo-derivatives were elucidated using a combination of NMR spectroscopic methods and X-ray crystal structure analyses.
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spelling pubmed-96640442022-11-14 Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine Ubaidullaev, A. U. Vinogradova, V. I. Zhurakulov, Sh. N. Mukarramov, N. I. Bobakulov, Kh. M. Turgunov, K. A. Tashkhodzhaev, B. Chem Nat Compd Article Bromination of the furanoquinoline alkaloid haplophyllidine by molecular bromine and N-bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The structures and absolute configurations of the chiral centers of all four bromo-derivatives were elucidated using a combination of NMR spectroscopic methods and X-ray crystal structure analyses. Springer US 2022-11-15 2022 /pmc/articles/PMC9664044/ /pubmed/36406158 http://dx.doi.org/10.1007/s10600-022-03877-6 Text en © Springer Science+Business Media, LLC, part of Springer Nature 2022, Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.
spellingShingle Article
Ubaidullaev, A. U.
Vinogradova, V. I.
Zhurakulov, Sh. N.
Mukarramov, N. I.
Bobakulov, Kh. M.
Turgunov, K. A.
Tashkhodzhaev, B.
Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine
title Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine
title_full Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine
title_fullStr Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine
title_full_unstemmed Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine
title_short Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine
title_sort intramolecular cyclization during bromination of the quinoline alkaloid haplophyllidine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9664044/
https://www.ncbi.nlm.nih.gov/pubmed/36406158
http://dx.doi.org/10.1007/s10600-022-03877-6
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