A new concise and enantiocontrolled total synthesis of (+)-ipomeamarone (1), a well-known phytoalexin, is described. The key step involved a tetrahydrofuran ring construction from optically active furyl alcohol 5 via the pi-allyl palladium complex with a chiral phosphine ligand. This procedure was also applicable to the synthesis of (-)-ngaione (2) and its stereoisomers.