Structure of ramulosin, a metabolic product of the fungus Pestalotia ramulosa

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Abstract
Ramulosin, a C10H14O3 metabolic product of the fungus P. ramulosa, gave UV-asborption and infrared-absorption spectra that indicated the presence of a [beta] -oxo iactone grouping. This grouping was confirmed by the liberation of 1 mole of carbon dioxide on hydrolysis. The formation of a copper chelate salt showed that the 2 functional groups are not in the same ring. These findings and a consideration of the structures of analogous fermentation products suggested that ramulosin is the enol chelate of perhydro-3-methyl-l,8-dioxo-2-benzopyran. This structure was confirmed by the conversion of ramulosin into a C9H16O2 ketol, which yielded the expected 1 -cyclohexyl propan-2-ol on removal of the carbonyl group.