Catalytic Asymmetric Formal Total Synthesis of (?)-Triptophenolide and (+)-Triptolide

摘要

Catalytic asymmetric formal synthesis of (?)-Triptophenolide and (+)-Triptolide have been achieved. Key reaction involves Palladium catalyzed asymmetric conjugate addition of aryl boronic acid to 3-methyl cyclohexe-1-none to form quaternary carbon. Claisen rearrangement and subsequent aldol reaction furnished trans-decaline key intermediate, which assured a formal total synthesis of (?)-Triptophenolide and (+)-Triptolide.Graphical Abstract