Total Synthesis of Salviachinensine A Using a Matteson Homologation Approach

Abstract

Salviachinensine A, a natural product obtained from the Chinese medicinal plant Salvia chinensis, was synthesised for the first time by employing Donald Matteson’s boronic ester homologation. The use of (R,R)‐dicyclohexylethane‐1,2‐diol (DICHED) enabled the generation of the required stereogenic centres in a highly stereoselective fashion. Salviachinensine A was formed in a one‐pot protecting group cleavage/lactonisation/ intramolecular Friedel‐Crafts alkylation, followed by Lewis acid‐catalysed cleavage of the acetal protecting groups.