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 <b>1</b> via an optimized synthetic route. Compound <b>1</b> was readily obtained in 11 steps and 11% overall yield on a gram scale from commerci...

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Bibliographic Details
Published in:Molecules
Main Authors: Taewoo Kim, Hyun Su Kim, Jaebong Jang, Dong-Jun Kim, Jongkook Lee, Dongjoo Lee, Seok-Ho Kim
Format: Article
Language:English
Published: MDPI AG 2022-10-01
Subjects:
phytoestrogen
isoflavanone
<i>Dalbergia oliveri</i>
hair growth
deoxybenzoin
total synthesis
Online Access:https://www.mdpi.com/1420-3049/27/19/6660
Description
Summary:This paper reports a concise and scalable method for the synthesis of the phytoestrogen 7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone <b>1</b> via an optimized synthetic route. Compound <b>1</b> 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.
ISSN:1420-3049

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