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Total Synthesis of Phorbazole B
Phorbazoles are polychlorinated heterocyclic secondary metabolites isolated from a marine sponge and several of these natural products have shown inhibitory activity against cancer cells. In this work, a synthesis of the trichlorinated phorbazole B using late stage electrophilic chlorination was dev...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7588006/ https://www.ncbi.nlm.nih.gov/pubmed/33096668 http://dx.doi.org/10.3390/molecules25204848 |
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author | Guttormsen, Yngve Fairhurst, Magnus E. Pandey, Sunil K. Isaksson, Johan Haug, Bengt Erik Bayer, Annette |
author_facet | Guttormsen, Yngve Fairhurst, Magnus E. Pandey, Sunil K. Isaksson, Johan Haug, Bengt Erik Bayer, Annette |
author_sort | Guttormsen, Yngve |
collection | PubMed |
description | Phorbazoles are polychlorinated heterocyclic secondary metabolites isolated from a marine sponge and several of these natural products have shown inhibitory activity against cancer cells. In this work, a synthesis of the trichlorinated phorbazole B using late stage electrophilic chlorination was developed. The synthesis relied on the use of an oxazole precursor, which was protected with an iodine in the reactive 4-position, followed by complete chlorination of all pyrrole positions. Attempts to prepare phorbazole A and C, which contain a 3,4-dichlorinated pyrrole, were unsuccessful as the desired chlorination pattern on the pyrrole could not be obtained. The identities of the dichlorinated intermediates and products were determined using NMR techniques including NOESY/ROESY, 1,1-ADEQUATE and high-resolution CLIP-HSQMBC. |
format | Online Article Text |
id | pubmed-7588006 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-75880062020-10-29 Total Synthesis of Phorbazole B Guttormsen, Yngve Fairhurst, Magnus E. Pandey, Sunil K. Isaksson, Johan Haug, Bengt Erik Bayer, Annette Molecules Article Phorbazoles are polychlorinated heterocyclic secondary metabolites isolated from a marine sponge and several of these natural products have shown inhibitory activity against cancer cells. In this work, a synthesis of the trichlorinated phorbazole B using late stage electrophilic chlorination was developed. The synthesis relied on the use of an oxazole precursor, which was protected with an iodine in the reactive 4-position, followed by complete chlorination of all pyrrole positions. Attempts to prepare phorbazole A and C, which contain a 3,4-dichlorinated pyrrole, were unsuccessful as the desired chlorination pattern on the pyrrole could not be obtained. The identities of the dichlorinated intermediates and products were determined using NMR techniques including NOESY/ROESY, 1,1-ADEQUATE and high-resolution CLIP-HSQMBC. MDPI 2020-10-21 /pmc/articles/PMC7588006/ /pubmed/33096668 http://dx.doi.org/10.3390/molecules25204848 Text en © 2020 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Guttormsen, Yngve Fairhurst, Magnus E. Pandey, Sunil K. Isaksson, Johan Haug, Bengt Erik Bayer, Annette Total Synthesis of Phorbazole B |
title | Total Synthesis of Phorbazole B |
title_full | Total Synthesis of Phorbazole B |
title_fullStr | Total Synthesis of Phorbazole B |
title_full_unstemmed | Total Synthesis of Phorbazole B |
title_short | Total Synthesis of Phorbazole B |
title_sort | total synthesis of phorbazole b |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7588006/ https://www.ncbi.nlm.nih.gov/pubmed/33096668 http://dx.doi.org/10.3390/molecules25204848 |
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