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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 |
Sumario: | 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. |
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