Total synthesis of tanzawaic acid A

The total synthesis of tanzawaic acid A, a potent antifungal active against Rhizopus oryzae, has been achieved. Key features of the synthetic strategy include the Heck reaction between a sterically hindered triflate and methyl acrylate and Evans alkylation/Friedel–Crafts acylation/stereoselective hydrogenation for the stereoselective construction of the triflate with a tetrahydronaphthalene unit. The practical total synthesis provided tanzawaic acid A with an overall yield of 29% over 20 steps.