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Synthesis and Bioactivity of Ophiofuranones A and B.

Franziska GillschHaoxuan ZengSofia I BärHedda SchreyRainer Schobert
Published in: The Journal of organic chemistry (2022)
Ophiofuranones A and B, metabolites of the fungus Ophiosphaerella korrae , were synthesized in 16 steps and 12%/22% yield. The stereogenic centers were established by Sharpless dihydroxylations and epoxidation, the 1,3-dienes via Wittig or HWE olefinations. The rings were closed through Knoevenagel-type condensation and lactonization. The ophiofuranones proved nontoxic at relevant concentrations against tumor cells, fibroblasts, and various bacteria and fungi. Ophiofuranone A and the monocyclic precursors 4 were weakly active against microbial biofilms.
Keyphrases
  • microbial community
  • ms ms
  • candida albicans
  • extracellular matrix