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Synthesis of Desepoxy‐Tedanolide C
The synthesis of desepoxy‐tedanolide C was accomplished and provided experimental evidence on the configuration of tedanolide C. The reported chemical shifts and coupling constants point to a configuration different from the published structure and analogous to the structures of the other members of...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251979/ https://www.ncbi.nlm.nih.gov/pubmed/33769622 http://dx.doi.org/10.1002/chem.202100553 |
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author | Lücke, Daniel Kalesse, Markus |
author_facet | Lücke, Daniel Kalesse, Markus |
author_sort | Lücke, Daniel |
collection | PubMed |
description | The synthesis of desepoxy‐tedanolide C was accomplished and provided experimental evidence on the configuration of tedanolide C. The reported chemical shifts and coupling constants point to a configuration different from the published structure and analogous to the structures of the other members of this family of natural products. The key step is a Kiyooka aldol protocol for the stereoselective synthesis of the tertiary alcohol flanked by three additional oxygenated carbon atoms. Furthermore, two additional aldol reactions and a Julia–Kocienski olefination were used to assemble the carbon framework. |
format | Online Article Text |
id | pubmed-8251979 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-82519792021-07-07 Synthesis of Desepoxy‐Tedanolide C Lücke, Daniel Kalesse, Markus Chemistry Communications The synthesis of desepoxy‐tedanolide C was accomplished and provided experimental evidence on the configuration of tedanolide C. The reported chemical shifts and coupling constants point to a configuration different from the published structure and analogous to the structures of the other members of this family of natural products. The key step is a Kiyooka aldol protocol for the stereoselective synthesis of the tertiary alcohol flanked by three additional oxygenated carbon atoms. Furthermore, two additional aldol reactions and a Julia–Kocienski olefination were used to assemble the carbon framework. John Wiley and Sons Inc. 2021-04-09 2021-04-26 /pmc/articles/PMC8251979/ /pubmed/33769622 http://dx.doi.org/10.1002/chem.202100553 Text en © 2021 The Authors. Published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Communications Lücke, Daniel Kalesse, Markus Synthesis of Desepoxy‐Tedanolide C |
title | Synthesis of Desepoxy‐Tedanolide C |
title_full | Synthesis of Desepoxy‐Tedanolide C |
title_fullStr | Synthesis of Desepoxy‐Tedanolide C |
title_full_unstemmed | Synthesis of Desepoxy‐Tedanolide C |
title_short | Synthesis of Desepoxy‐Tedanolide C |
title_sort | synthesis of desepoxy‐tedanolide c |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251979/ https://www.ncbi.nlm.nih.gov/pubmed/33769622 http://dx.doi.org/10.1002/chem.202100553 |
work_keys_str_mv | AT luckedaniel synthesisofdesepoxytedanolidec AT kalessemarkus synthesisofdesepoxytedanolidec |