This paper describes a new approach for the enantioselective syntheses of naturally occurring polyhydroxylated dihydroagarofuran sesquiterpenoids starting from (−)-carvone. Through utilizing asymmetric Robinson annulation and acetoxylation as key steps, the agarofuran skeleton was enantioselectively constructed and an oxyfunctionalized group was introduced into the C-1 position. The important intermediate 23 to dihydroagarofuran was obtained in eleven steps.