Cargando…
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...
Autores principales: | , , , |
---|---|
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 |
_version_ | 1782491748922032128 |
---|---|
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. |
format | Online Article Text |
id | pubmed-5215369 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT geddisstephenm divergentsynthesisofquinolonenaturalproductsfrompseudonocardiaspcl38489 AT carrolaura divergentsynthesisofquinolonenaturalproductsfrompseudonocardiaspcl38489 AT hodgkinsonjamest divergentsynthesisofquinolonenaturalproductsfrompseudonocardiaspcl38489 AT springdavidr divergentsynthesisofquinolonenaturalproductsfrompseudonocardiaspcl38489 |