A partial bioinspired as well as the total synthesis of archazolid F, a highly potent V-ATPase inhibitory, antiproliferative polyketide macrolide, is described. Key features of the synthetic routes include a highly stereoselective aldol condensation of two elaborate fragments and macrocyclizations either by a Shiina macrolactonization or by a challenging RCM reaction of an octaene substrate. The syntheses unequivocally confirm the full architecture of this very scarce archazolid.
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