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Stereodivergent Total Syntheses of (+)‐Mycaperoxides C, D, G Methyl Ester and (−)‐Mycaperoxide B
Mycaperoxides are natural endoperoxides isolated from different Mycale genus sponges, showing significant antiviral or antibacterial activities. We report herein the first total syntheses of representative congeners of this family from sclareol using a stereodivergent approach. Thus, an innovative o...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107902/ https://www.ncbi.nlm.nih.gov/pubmed/36305658 http://dx.doi.org/10.1002/chem.202203004 |
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author | Kerim, Mansour D. Evanno, Laurent Ferrié, Laurent |
author_facet | Kerim, Mansour D. Evanno, Laurent Ferrié, Laurent |
author_sort | Kerim, Mansour D. |
collection | PubMed |
description | Mycaperoxides are natural endoperoxides isolated from different Mycale genus sponges, showing significant antiviral or antibacterial activities. We report herein the first total syntheses of representative congeners of this family from sclareol using a stereodivergent approach. Thus, an innovative oxidative ring expansion of cyclobutanol was used to bring the 1,2‐dioxane subunit, and a Mukaiyama aldol reaction on peroxycarbenium species was utilized to install the propionic acid subunit. During the study toward (+)‐mycaperoxide D methyl ester (2), the isolation of the eight possible diastereomers under their ethyl thioester form allowed to build a pertinent database for further NMR assignment studies. Thus, we completed the total syntheses of (+)‐mycaperoxides D, C, G methyl ester, and (−)‐mycaperoxide B in 11 to 15 steps, confirming their original assignment. |
format | Online Article Text |
id | pubmed-10107902 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-101079022023-04-18 Stereodivergent Total Syntheses of (+)‐Mycaperoxides C, D, G Methyl Ester and (−)‐Mycaperoxide B Kerim, Mansour D. Evanno, Laurent Ferrié, Laurent Chemistry Research Articles Mycaperoxides are natural endoperoxides isolated from different Mycale genus sponges, showing significant antiviral or antibacterial activities. We report herein the first total syntheses of representative congeners of this family from sclareol using a stereodivergent approach. Thus, an innovative oxidative ring expansion of cyclobutanol was used to bring the 1,2‐dioxane subunit, and a Mukaiyama aldol reaction on peroxycarbenium species was utilized to install the propionic acid subunit. During the study toward (+)‐mycaperoxide D methyl ester (2), the isolation of the eight possible diastereomers under their ethyl thioester form allowed to build a pertinent database for further NMR assignment studies. Thus, we completed the total syntheses of (+)‐mycaperoxides D, C, G methyl ester, and (−)‐mycaperoxide B in 11 to 15 steps, confirming their original assignment. John Wiley and Sons Inc. 2022-12-07 2023-01-27 /pmc/articles/PMC10107902/ /pubmed/36305658 http://dx.doi.org/10.1002/chem.202203004 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Research Articles Kerim, Mansour D. Evanno, Laurent Ferrié, Laurent Stereodivergent Total Syntheses of (+)‐Mycaperoxides C, D, G Methyl Ester and (−)‐Mycaperoxide B |
title | Stereodivergent Total Syntheses of (+)‐Mycaperoxides C, D, G Methyl Ester and (−)‐Mycaperoxide B
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title_full | Stereodivergent Total Syntheses of (+)‐Mycaperoxides C, D, G Methyl Ester and (−)‐Mycaperoxide B
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title_fullStr | Stereodivergent Total Syntheses of (+)‐Mycaperoxides C, D, G Methyl Ester and (−)‐Mycaperoxide B
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title_full_unstemmed | Stereodivergent Total Syntheses of (+)‐Mycaperoxides C, D, G Methyl Ester and (−)‐Mycaperoxide B
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title_short | Stereodivergent Total Syntheses of (+)‐Mycaperoxides C, D, G Methyl Ester and (−)‐Mycaperoxide B
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title_sort | stereodivergent total syntheses of (+)‐mycaperoxides c, d, g methyl ester and (−)‐mycaperoxide b |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107902/ https://www.ncbi.nlm.nih.gov/pubmed/36305658 http://dx.doi.org/10.1002/chem.202203004 |
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