Total syntheses of surinone B, alatanones A-B, and trineurone A.

ABSTRACT

The total syntheses of four polyketides, surinone B (1), alatanones A-B (2-3), and trineurone A (4) were accomplished through an efficient and unified strategy via one-pot C-acylation reaction coupling 1,3-cyclohexadiones with EDC-activated acids under mild conditions. Alatanone A (2) was found to be a potent anti-microbial agent against Gram-positive and Gram-negative bacteria with MIC 31.25 µg/ml while alatanone B (3) was found to be a potent anti-fungal agent against Cladosporium cladosporioides with MIC 62.5 µg/ml compared to cycloheximide MIC 125 µg/ml. Our methodology allows performing kilogram scale of these scarce polyketides for the development of new antimicrobials.