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A chemoenzymatic approach to the title framework is reported. The reaction sequence starts with the whole-cell biotransformation of iodobenzene and the conversion of the resulting homochiral metabolite into a triene that engages in an intramolecular Diels–Alder reaction and so affording an adduct embodying the platencin core. Application of an oxa-di-π-methane rearrangement to a derivative of this core affords a cyclopropannulated form of the target framework; the latter is then obtained through a TMSI-mediated cleavage of the three-membered ring. A strategy for the assembly of the enantiomeric framework is also described.