Synthesis and Bioactivity of Ophiofuranones A and B

Ophiofuranones A and B, metabolites of the fungusOphiosphaerellakorrae, were synthesized in 16 steps and 12%/22% yield. The stereogenic centers wereestablished by Sharpless dihydroxylations and epoxidation, the 1,3-dienes via Wittig orHWE olefinations. The rings were closed through Knoevenagel-type condensation andlactonization. The ophiofuranones proved nontoxic at relevant concentrations againsttumor cells,fibroblasts, and various bacteria and fungi. Ophiofuranone A and themonocyclic precursors4were weakly active against microbial biofilms.

Automated summary

This study successfully synthesized the metabolites of Ophiosphaerella korrae, Ophiofuranones A and B. The compounds were found to be non-toxic against tumor cells, fibroblasts, and various bacteria and fungi at relevant concentrations.