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Incubation of recombinant elaiophylin thioesterase\/cyclase with a synthetic pentaketide analogue of the presumed monomeric polyketide precursor of elaiophylin, specifically its <jats:italic>N<\/jats:italic>\u2010acetylcysteamine thioester, produced a novel 16\u2010membered C<jats:sub>2<\/jats:sub>\u2010symmetric macrodiolide. A linear dimeric thioester is an intermediate in ring formation, which indicates iterative use of the thioesterase active site in ligation and subsequent cyclization. Furthermore, the elaiophylin thioesterase acts on a mixture of pentaketide and tetraketide thioesters to give both the symmetric decaketide diolide and the novel asymmetric hybrid nonaketide diolide. 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