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The biosynthesis of the meroterpenoid neomarinone from a marine actinomycete was probed through feeding experiments with ¹³C-labeled precursors. NMR characterization of [U-¹³C6]glucose-enriched neomarinone led to the structural revision of structure 4a to 4b, which was confirmed by extensive 2D NMR spectrometry with unlabeled compound.

A mutational analysis of the enterocin biosynthesis genes revealed that the putative oxygenase and the methyltransferase gene products EncM and EncK, respectively, jointly catalyze a biosynthetic Favorskii-like rearrangement. Inactivation of either gene terminated enterocin production and caused the accumulation of four nonrearranged, nonmethylated polyketides. The structure elucidation of the new wailupemycins E−G is reported.