Total Syntheses of Linear Polythiazole/Oxazole Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B**

Plantazolicin A, a linear decacyclic natural product, exhibits desirable selective activity against the causative agent of anthrax toxicity. The total synthesis of plantazolicin A and its biosynthetic precursor plantazolicin B was successfully achieved by an efficient, unified, and highly convergent...

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Detalles Bibliográficos
Autores principales: Wilson, Zoe E, Fenner, Sabine, Ley, Steven V
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4464531/
https://www.ncbi.nlm.nih.gov/pubmed/25424526
http://dx.doi.org/10.1002/anie.201410063
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author Wilson, Zoe E
Fenner, Sabine
Ley, Steven V
author_facet Wilson, Zoe E
Fenner, Sabine
Ley, Steven V
author_sort Wilson, Zoe E
collection PubMed
description Plantazolicin A, a linear decacyclic natural product, exhibits desirable selective activity against the causative agent of anthrax toxicity. The total synthesis of plantazolicin A and its biosynthetic precursor plantazolicin B was successfully achieved by an efficient, unified, and highly convergent route featuring dicyclizations to form 2,4-concatenated oxazoles and the mild synthesis of thiazoles from natural amino acids. This report represents the first synthesis of plantazolicin B and includes the first complete characterization data for both natural products.
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spelling pubmed-44645312015-06-17 Total Syntheses of Linear Polythiazole/Oxazole Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B** Wilson, Zoe E Fenner, Sabine Ley, Steven V Angew Chem Int Ed Engl Communications Plantazolicin A, a linear decacyclic natural product, exhibits desirable selective activity against the causative agent of anthrax toxicity. The total synthesis of plantazolicin A and its biosynthetic precursor plantazolicin B was successfully achieved by an efficient, unified, and highly convergent route featuring dicyclizations to form 2,4-concatenated oxazoles and the mild synthesis of thiazoles from natural amino acids. This report represents the first synthesis of plantazolicin B and includes the first complete characterization data for both natural products. WILEY-VCH Verlag 2015-01-19 2014-11-25 /pmc/articles/PMC4464531/ /pubmed/25424526 http://dx.doi.org/10.1002/anie.201410063 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by/3.0/ This is an open access article under the terms of the Creative Commons Attribution Non-Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Wilson, Zoe E
Fenner, Sabine
Ley, Steven V
Total Syntheses of Linear Polythiazole/Oxazole Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B**
title Total Syntheses of Linear Polythiazole/Oxazole Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B**
title_full Total Syntheses of Linear Polythiazole/Oxazole Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B**
title_fullStr Total Syntheses of Linear Polythiazole/Oxazole Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B**
title_full_unstemmed Total Syntheses of Linear Polythiazole/Oxazole Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B**
title_short Total Syntheses of Linear Polythiazole/Oxazole Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B**
title_sort total syntheses of linear polythiazole/oxazole plantazolicin a and its biosynthetic precursor plantazolicin b**
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4464531/
https://www.ncbi.nlm.nih.gov/pubmed/25424526
http://dx.doi.org/10.1002/anie.201410063
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