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. 2024;72(6):570-573.
doi: 10.1248/cpb.c24-00276.

Total Synthesis of (+)-Silybin A

Makoto Inai  1 , Hiroto Sagara  1 , Yoshinori Ueno  1 , Hitoshi Ouchi  1 , Fumihiko Yoshimura  1 , Tomohiro Asakawa  2 , Yoshitaka Hamashima  1 , Toshiyuki Kan  1
Affiliations
Free article

Total Synthesis of (+)-Silybin A

Makoto Inai et al. Chem Pharm Bull (Tokyo). 2024.
Free article

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.

Keywords: hybrid polyphenol; modified Julia–Kocienski olefination; quinomethide; silybin A; total synthesis.

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