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Updated: Sep 25, 2025

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Synthesis and Bioactivity of Ophiofuranones A and B
Franziska Gillsch1, Haoxuan Zeng2, Sofia I Bär1
1Organic Chemistry Laboratory, University Bayreuth, Universitaetsstraße 30, 95440 Bayreuth, Germany.
Abstract:
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.
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