Total Synthesis of Salviachinensine A Using a Matteson Homologation Approach

Salviachinensine A, a natural product obtained from the Chinese medicinal plant Salvia chinensis , was synthesized 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 centers in a highly stereoselective fashion. Salviachinensine A was formed in a one‐pot protecting group cleavage/lactonization/ intramolecular Friedel–Crafts alkylation, followed by Lewis acid‐catalysed cleavage of the acetal protecting groups.