Asymmetric Total Synthesis of Hispidanin A

Abstract

Asymmetric total synthesis of the dimeric diterpenoid hispidanin A was accomplished by non-catalytic Diels-Alder cycloaddition at room temperature. The synthesis relies on iron-catalyzed coupling to construct a Z-configured trisubstituted alkene, an iron-catalyzed radical cascade to generate a labdane-type diene, and both Yamamoto cationic polyene cyclization and palladium-catalyzed Stille coupling to generate a totarane-type dienophile.