Enantioselective Total Synthesis of (+)-Eutypoxide B

The enantioselective synthesis of (+)-eutypoxide B, a metabolite isolated from the culture medium of the fungus Eutypa lata, is described. Two highly stereoselective and efficient sequencial 1,4-additions to enone systems, derived from d-(−)-quinic acid, are the key to the synthesis. The synthesis of a diastereoisomer of (+)-eutypoxide B, was also accomplished.