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.

Keywords:

• Polyketides
• surinone B
• alatanones A–B
• trineurone A
• C-acylation
• antimicrobial screening

Acknowledgement

We are thankful to director, Dr. S. Chandrasekhar, IICT for constant support and UGC for awarding SRF to NRG.