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Total syntheses of surinone B, alatanones A–B, and trineurone A

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posted on 2018-04-23, 16:55 authored by Narayana Rao Gundoju, Ramesh Bokam, Nageswara Rao Yalavarthi, Sudheer Kumar Buddana, R. S. Prakasham, Mangala Gowri Ponnapalli

The total syntheses of four polyketides, surinone B (1), alatanones A–B (23), 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.

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