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Total Synthesis of (+)-Silybin A.
Inai, Makoto; Sagara, Hiroto; Ueno, Yoshinori; Ouchi, Hitoshi; Yoshimura, Fumihiko; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki.
Affiliation
  • Inai M; School of Pharmaceutical Sciences, University of Shizuoka.
  • Sagara H; School of Pharmaceutical Sciences, University of Shizuoka.
  • Ueno Y; School of Pharmaceutical Sciences, University of Shizuoka.
  • Ouchi H; School of Pharmaceutical Sciences, University of Shizuoka.
  • Yoshimura F; School of Pharmaceutical Sciences, University of Shizuoka.
  • Asakawa T; School of Marine Science and Technology, Tokai University.
  • Hamashima Y; School of Pharmaceutical Sciences, University of Shizuoka.
  • Kan T; School of Pharmaceutical Sciences, University of Shizuoka.
Chem Pharm Bull (Tokyo) ; 72(6): 570-573, 2024.
Article in En | MEDLINE | ID: mdl-38910121
ABSTRACT
We report the first total synthesis of silybin A (1). Key synthetic steps include the construction of the 1,4-benzodioxane neolignan skeleton, a modified Julia-Kocienski olefination reaction between m-nitrophenyltetrazole sulfone (m-NPT sulfone) 10 and aldehyde 21, the formation of the flavanol lignan skeleton 28 via a quinomethide intermediate under acidic conditions, and stepwise oxidation of the benzylic position of flavanol 29.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Silybin Language: En Journal: Chem Pharm Bull (Tokyo) Year: 2024 Type: Article
Fulltext
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PubMed Links
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Silybin Language: En Journal: Chem Pharm Bull (Tokyo) Year: 2024 Type: Article