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Synthesis of 7,2′-Dihydroxy-4′,5′-Dimethoxyisoflavanone, a Phytoestrogen with Derma Papilla Cell Proliferative Activity
This paper reports a concise and scalable method for the synthesis of the phytoestrogen 7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone 1 via an optimized synthetic route. Compound 1 was readily obtained in 11 steps and 11% overall yield on a gram scale from commercially available 3,4-dimethoxyphenol. Th...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9572366/ https://www.ncbi.nlm.nih.gov/pubmed/36235197 http://dx.doi.org/10.3390/molecules27196660 |
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author | Kim, Taewoo Kim, Hyun Su Jang, Jaebong Kim, Dong-Jun Lee, Jongkook Lee, Dongjoo Kim, Seok-Ho |
author_facet | Kim, Taewoo Kim, Hyun Su Jang, Jaebong Kim, Dong-Jun Lee, Jongkook Lee, Dongjoo Kim, Seok-Ho |
author_sort | Kim, Taewoo |
collection | PubMed |
description | This paper reports a concise and scalable method for the synthesis of the phytoestrogen 7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone 1 via an optimized synthetic route. Compound 1 was readily obtained in 11 steps and 11% overall yield on a gram scale from commercially available 3,4-dimethoxyphenol. The key features of the synthesis include the construction of the deoxybenzoin unit through a sequence of Claisen rearrangement, oxidative cleavage, and aryllithium addition and the efficient synthesis of the isoflavanone architecture from highly functionalized 2-hydroxyketone. |
format | Online Article Text |
id | pubmed-9572366 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-95723662022-10-17 Synthesis of 7,2′-Dihydroxy-4′,5′-Dimethoxyisoflavanone, a Phytoestrogen with Derma Papilla Cell Proliferative Activity Kim, Taewoo Kim, Hyun Su Jang, Jaebong Kim, Dong-Jun Lee, Jongkook Lee, Dongjoo Kim, Seok-Ho Molecules Communication This paper reports a concise and scalable method for the synthesis of the phytoestrogen 7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone 1 via an optimized synthetic route. Compound 1 was readily obtained in 11 steps and 11% overall yield on a gram scale from commercially available 3,4-dimethoxyphenol. The key features of the synthesis include the construction of the deoxybenzoin unit through a sequence of Claisen rearrangement, oxidative cleavage, and aryllithium addition and the efficient synthesis of the isoflavanone architecture from highly functionalized 2-hydroxyketone. MDPI 2022-10-07 /pmc/articles/PMC9572366/ /pubmed/36235197 http://dx.doi.org/10.3390/molecules27196660 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Communication Kim, Taewoo Kim, Hyun Su Jang, Jaebong Kim, Dong-Jun Lee, Jongkook Lee, Dongjoo Kim, Seok-Ho Synthesis of 7,2′-Dihydroxy-4′,5′-Dimethoxyisoflavanone, a Phytoestrogen with Derma Papilla Cell Proliferative Activity |
title | Synthesis of 7,2′-Dihydroxy-4′,5′-Dimethoxyisoflavanone, a Phytoestrogen with Derma Papilla Cell Proliferative Activity |
title_full | Synthesis of 7,2′-Dihydroxy-4′,5′-Dimethoxyisoflavanone, a Phytoestrogen with Derma Papilla Cell Proliferative Activity |
title_fullStr | Synthesis of 7,2′-Dihydroxy-4′,5′-Dimethoxyisoflavanone, a Phytoestrogen with Derma Papilla Cell Proliferative Activity |
title_full_unstemmed | Synthesis of 7,2′-Dihydroxy-4′,5′-Dimethoxyisoflavanone, a Phytoestrogen with Derma Papilla Cell Proliferative Activity |
title_short | Synthesis of 7,2′-Dihydroxy-4′,5′-Dimethoxyisoflavanone, a Phytoestrogen with Derma Papilla Cell Proliferative Activity |
title_sort | synthesis of 7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone, a phytoestrogen with derma papilla cell proliferative activity |
topic | Communication |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9572366/ https://www.ncbi.nlm.nih.gov/pubmed/36235197 http://dx.doi.org/10.3390/molecules27196660 |
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