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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.
Afiliação
  • Kim T; College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon-si, Gyeonggi-do 11160, Korea.
  • Kim HS; College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon-si, Gyeonggi-do 11160, Korea.
  • Jang J; College of Pharmacy, Korea University, Sejong 30019, Korea.
  • Kim DJ; College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon-si, Gyeonggi-do 11160, Korea.
  • Lee J; College of Pharmacy, Kangwon National University, Chuncheon, Gangwon-do 24341, Korea.
  • Lee D; College of Pharmacy and Research Institute of Pharmaceutical Science and Technology (RIPST), Ajou University, 206 Worldcup-ro, Yeongtong-gu, Suwon 16499, Korea.
  • Kim SH; College of Pharmacy, Kangwon National University, Chuncheon, Gangwon-do 24341, Korea.
Molecules ; 27(19)2022 Oct 07.
Article em En | MEDLINE | ID: mdl-36235197
ABSTRACT
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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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Fitoestrógenos Idioma: En Revista: Molecules Assunto da revista: BIOLOGIA Ano de publicação: 2022 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Fitoestrógenos Idioma: En Revista: Molecules Assunto da revista: BIOLOGIA Ano de publicação: 2022 Tipo de documento: Article