Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 9, Pages 6520-6523Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00521
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- Ministry for Science & Culture of the German State of Lower Saxony (MWK) [21-78904-63-5/19]
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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.
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.
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