3 years ago

Oxidation of the Meroterpenoid (−)-Terreumol C from the Mushroom Tricholoma terreum: Discovery of Cytotoxic Analogues

Oxidation of the Meroterpenoid (−)-Terreumol C from the Mushroom Tricholoma terreum: Discovery of Cytotoxic Analogues
Alex Frichert, Thomas Lindel, Mark Brönstrup, Peter G. Jones
Aiming at the discovery of new cytotoxic meroterpenoids, the chemical reactivity of the natural product (−)-terreumol C from the edible mushroom Tricholoma terreum was investigated. A series of high-yielding oxygenations and brominations at the 10-membered ring were discovered. The regioselectivity of hydroxylation could be guided by installing protecting groups at the hydroquinone section. Dihydroxylation led to the stereoselective formation of a novel tricycle containing an 11-oxabicyclo[5.3.1]undecane system. Several of the compounds proved to be as cytotoxic against cancer cell lines as the natural products terreumols A and C in the single-digit micromolar range. Interestingly, functionalization of the southern rim formed by carbons C5–C6–C7–C8 is tolerated without much loss of cytotoxicity.

Publisher URL: http://dx.doi.org/10.1021/acs.jnatprod.7b00236

DOI: 10.1021/acs.jnatprod.7b00236

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