iiinova — where your digital self keeps evolving

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Anders Kiib @aekiib.bsky.social · 30/01/2025

Background: Cyclohelminthol I-IV were first isolated from Helminthosporium velutinum yone96 by the Hashimoto group in 2016 (doi.org/10.1016/j.te... ). Given our interest in natural products and interesting electrophiles, we set out to develop syntheses for CHM-I-IV. 2/7

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Anders Kiib @aekiib.bsky.social · 30/01/2025

The synthesis was conducted by fellow PhD student in the group Thomas Terp Paulsen (who is not on BlueSky), and key steps in the syntheses were selective chlorinations (at C2 and C5) and a Ni-catalyzed reductive cross coupling between an enone, a vinyl bromide, and triethylsilyl chloride 3/7

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Anders Kiib @aekiib.bsky.social · 30/01/2025

Morphological profiling (cell painting) indicated that CHM-II was the most biologically active of the compounds, while simultaneously revealing strong morphological correlations to dimethyl fumarate and sulforaphane – both of which are known to act in a covalent manner. 4/7

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