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Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489

Two divergent synthetic routes are reported offering access to four quinolone natural products from Pseudonocardia sp. CL38489. Key steps to the natural products involved a regioselective epoxidation, an intramolecular Buchwald–Hartwig amination and a final acid‐catalysed 1,3‐allylic‐alcohol rearran...

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Autores principales: Geddis, Stephen M., Carro, Laura, Hodgkinson, James T., Spring, David R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5215369/
https://www.ncbi.nlm.nih.gov/pubmed/28111524
http://dx.doi.org/10.1002/ejoc.201601195
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author Geddis, Stephen M.
Carro, Laura
Hodgkinson, James T.
Spring, David R.
author_facet Geddis, Stephen M.
Carro, Laura
Hodgkinson, James T.
Spring, David R.
author_sort Geddis, Stephen M.
collection PubMed
description Two divergent synthetic routes are reported offering access to four quinolone natural products from Pseudonocardia sp. CL38489. Key steps to the natural products involved a regioselective epoxidation, an intramolecular Buchwald–Hartwig amination and a final acid‐catalysed 1,3‐allylic‐alcohol rearrangement to give two of the natural products in one step. This study completes the synthesis of all eight antibacterial quinolone natural products reported in the family. In addition, this modular strategy enables an improved synthesis towards two natural products previously reported.
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spelling pubmed-52153692017-01-18 Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489 Geddis, Stephen M. Carro, Laura Hodgkinson, James T. Spring, David R. European J Org Chem Communications Two divergent synthetic routes are reported offering access to four quinolone natural products from Pseudonocardia sp. CL38489. Key steps to the natural products involved a regioselective epoxidation, an intramolecular Buchwald–Hartwig amination and a final acid‐catalysed 1,3‐allylic‐alcohol rearrangement to give two of the natural products in one step. This study completes the synthesis of all eight antibacterial quinolone natural products reported in the family. In addition, this modular strategy enables an improved synthesis towards two natural products previously reported. John Wiley and Sons Inc. 2016-11-15 2016-12 /pmc/articles/PMC5215369/ /pubmed/28111524 http://dx.doi.org/10.1002/ejoc.201601195 Text en © 2016 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Geddis, Stephen M.
Carro, Laura
Hodgkinson, James T.
Spring, David R.
Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489
title Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489
title_full Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489
title_fullStr Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489
title_full_unstemmed Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489
title_short Divergent Synthesis of Quinolone Natural Products from Pseudonocardia sp. CL38489
title_sort divergent synthesis of quinolone natural products from pseudonocardia sp. cl38489
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5215369/
https://www.ncbi.nlm.nih.gov/pubmed/28111524
http://dx.doi.org/10.1002/ejoc.201601195
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