Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid

An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels‐Alder type cycloaddition using a chiral auxiliary. CFA and 6‐epi‐CFA were synthesized by hydro...

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Autores principales: Watanabe, Raku, Kato, Nobuki, Hayashi, Kengo, Tozawa, Sho, Ogura, Yusuke, Kuwahara, Shigefumi, Ueda, Minoru
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7545439/
https://www.ncbi.nlm.nih.gov/pubmed/33072470
http://dx.doi.org/10.1002/open.202000210
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author Watanabe, Raku
Kato, Nobuki
Hayashi, Kengo
Tozawa, Sho
Ogura, Yusuke
Kuwahara, Shigefumi
Ueda, Minoru
author_facet Watanabe, Raku
Kato, Nobuki
Hayashi, Kengo
Tozawa, Sho
Ogura, Yusuke
Kuwahara, Shigefumi
Ueda, Minoru
author_sort Watanabe, Raku
collection PubMed
description An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels‐Alder type cycloaddition using a chiral auxiliary. CFA and 6‐epi‐CFA were synthesized by hydrogenation of a common intermediate. During the synthesis of 6‐epi‐CFA, we established that its cis‐fused configuration is important for the introduction of C4‐C5 double bond by dehydration. This report is the first practical synthesis of both 6‐epi‐CFA, and its enantiomer.
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spelling pubmed-75454392020-10-16 Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid Watanabe, Raku Kato, Nobuki Hayashi, Kengo Tozawa, Sho Ogura, Yusuke Kuwahara, Shigefumi Ueda, Minoru ChemistryOpen Full Papers An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels‐Alder type cycloaddition using a chiral auxiliary. CFA and 6‐epi‐CFA were synthesized by hydrogenation of a common intermediate. During the synthesis of 6‐epi‐CFA, we established that its cis‐fused configuration is important for the introduction of C4‐C5 double bond by dehydration. This report is the first practical synthesis of both 6‐epi‐CFA, and its enantiomer. John Wiley and Sons Inc. 2020-10-09 /pmc/articles/PMC7545439/ /pubmed/33072470 http://dx.doi.org/10.1002/open.202000210 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ 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 Full Papers
Watanabe, Raku
Kato, Nobuki
Hayashi, Kengo
Tozawa, Sho
Ogura, Yusuke
Kuwahara, Shigefumi
Ueda, Minoru
Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid
title Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid
title_full Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid
title_fullStr Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid
title_full_unstemmed Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid
title_short Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid
title_sort stereoselective syntheses of all the possible stereoisomers of coronafacic acid
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7545439/
https://www.ncbi.nlm.nih.gov/pubmed/33072470
http://dx.doi.org/10.1002/open.202000210
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