Apiosporamide (1) was isolated from the fungus Apiospora montagnei Saccardo (Amphisphaeriaceae) in 1994, exhibiting potent antifungal activity against the coprophilous fungus Ascobolus furfuraceus and antibacterial activity against Bacillus subtilis and Staphylococcus aureus. Recently, the corresponding ketone YM-215343 (2) was identified and shown to demonstrate cytotoxicity against HeLa S3 cell cultures. Structural assignments of 1 (and 2) have proven challenging: although homonuclear and heteronuclear 2D NMR spectroscopic experiments permitted the assignment of the relative configuration of the decalin ring, the configuration of the epoxydiol system could not be determined unambiguously (tentatively assumed to have an all-syn topology); the trans decalin portion and cyclohexanediol moiety present independent 1H NMR spectroscopic systems due to the planarity of the central pyridinone linkage; and the substitution pattern of the pyridinone ring was assumed by comparison with the 13C NMR spectroscopic chemical shifts of 1 with ilicicolin H (previously described and confirmed by total synthesis as a 5-aryl-4-hydroxy-3-acyl-2-pyridone). Herein, we report a convergent total synthesis of (+)-apiosporamide (1) and its subsequent oxidation to yield YM-215343 (2). Our efforts have established the assignments of the relative and absolute configurations, which confirm the antipodal relationship of our synthetic materials with the naturally occurring metabolites.