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Starting with (S)‐ or (R)‐4‐Bromo‐1,2‐epoxybutane [commercially available or readily made from (S)‐ or (R)‐malic acid], both enantiomers of the germination self‐inhibitor gloeosporone were synthesized. The absolute configuration of the natural product was thus proven to be 4S,7R,13R. Microbiological studies showed that both enantiomers of the compound cause inhibition of germination in spores of Colletotrichum gloeosporioides, and that (‐)‐gloeosporone is also active against a variety of other fungi. In order to gain some insight into the mode of action, 23Na NMR measurements and ion‐selectivity studies were undertaken; none of these experiments provided evidence for a gloeosporone–metal ion interaction.

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