| Abstract
| - Permanganate oxidation of farnesoate esters 12a−d afforded perhydro-2,2‘-bifuranyl compounds16a−d, with control of relative stereochemistry at four new stereocenters. Subsequent oxidativecleavage of 16a−d then provided tetrahydrofuran-containing fragments 17a−d, one of them 17bpossessing the same relative stereochemistry present in the C13−C21 portion of the polyetherantibiotic semduramycin (1). Control of the absolute stereochemistry was achieved through theuse of the Oppolzer sultam chiral auxiliary. The requisite starting trienes were preparedstereoselectively in just three steps from geranyl chloride or neryl chloride, providing a short andversatile route to polyether fragments.
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