Concise Synthesis of Catechin Metabolites 5-(3′,4′-Dihydroxyphenyl)-γ-valerolactones (DHPV) in Optically Pure Form and Their Stereochemical Effects on Skin Wrinkle-Reducing Activities

oleh: Joonseong Hur, A-Ram Kim, Hyun Su Kim, Changjin Lim, Taewoo Kim, Tae-Aug Kim, Jaehoon Sim, Young-Ger Suh

Format: Article
Diterbitkan: MDPI AG 2020-04-01

Deskripsi

A concise and scalable synthetic route for optically pure (4<i>S</i>) and (4<i>R</i>)-5-(3′,4′-dihydroxyphenyl)-γ-valerolactones (DHPVs), catechin metabolites, has been developed via the efficient construction of a γ-valerolactone moiety from hexenol. Noticeably, the different skin wrinkle-reducing activities of each metabolite were revealed via our unique syntheses of DHPVs in an enantiomerically pure form.