Pamamycin-607 belongs to a group of homologous macrodiolides, produced by various “Streptomyces”, that possess remarkable autoregulatory antifungal, antibacterial and anion-transfering activities. The synthesis of the non-racemic C8–C18 portion of pamamycin-607 is reported here and involves a route that features a stereoselective aldol condensation followed by a stereocontrolled reductive amination of the aldol and a cis-selective tetrahydrofuran formation by an intramolecular Michael cyclization induced by the geometry of the substrate.
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Mandville et al. (1999) studied this question.