Total Synthesis of (+)-Silybin A.

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.

Citation

Makoto Inai, Hiroto Sagara, Yoshinori Ueno, Hitoshi Ouchi, Fumihiko Yoshimura, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan. Total Synthesis of (+)-Silybin A. Chemical & pharmaceutical bulletin. 2024;72(6):570-573

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PMID: 38910121

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