Total Synthesis of (±)-Spiroaxillarone A via a Reversible Sulfa-Michael Addition.

A bioinspired strategy is described for the total synthesis of spiroaxillarone A, which exhibited significant antimalarial activity against resistant Plasmodium falciparum (IC 50 = 2.32 μM). The key steps include an intermolecular ethanethiol Michael addition, o -quinone Michael addition, and subsequent β-ethanethiol elimination. This synthetic sequence provides a potential biosynthetic pathway of spiroaxillarone A.