Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Kim, Taewoo, Kim, Hyun Su, Jang, Jaebong, Kim, Dong-Jun, Lee, Jongkook, Lee, Dongjoo, Kim, Seok-Ho
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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
_version_ 1784810595858513920
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
work_keys_str_mv AT kimtaewoo synthesisof72dihydroxy45dimethoxyisoflavanoneaphytoestrogenwithdermapapillacellproliferativeactivity
AT kimhyunsu synthesisof72dihydroxy45dimethoxyisoflavanoneaphytoestrogenwithdermapapillacellproliferativeactivity
AT jangjaebong synthesisof72dihydroxy45dimethoxyisoflavanoneaphytoestrogenwithdermapapillacellproliferativeactivity
AT kimdongjun synthesisof72dihydroxy45dimethoxyisoflavanoneaphytoestrogenwithdermapapillacellproliferativeactivity
AT leejongkook synthesisof72dihydroxy45dimethoxyisoflavanoneaphytoestrogenwithdermapapillacellproliferativeactivity
AT leedongjoo synthesisof72dihydroxy45dimethoxyisoflavanoneaphytoestrogenwithdermapapillacellproliferativeactivity
AT kimseokho synthesisof72dihydroxy45dimethoxyisoflavanoneaphytoestrogenwithdermapapillacellproliferativeactivity