Synthetic study of tautomycin. Part 2: Synthesis of Ichiharaʹs fragment based on regioselective enzymatic acetylation of complex molecule

Formal synthesis of tautomycin, which inhibits type 1 and type 2A protein phosphatases, was achieved. Spiroketal diol was synthesized from alcohol or . The regioselective enzymatic acetylation of with the lipase ‘Amano PS’ gave monoacetate in 90% yield, which was converted into Ichiharaʹs intermediate based on Julia coupling and Wittig homologation.