Abstract
The total synthesis of (S)-stigmolone, a pheromone from the myxobacterium Stigmatella aurantiaca that induces the formation of fruiting bodies, is described. Sharpless asymmetric epoxidation followed by tert-butyldimethylsilyl trifluoromethanesulfonate/Hunig’s base mediated intramolecular hydride ion transfer reactions were used to install the C-5 stereogenic center. Commercially available isovaleraldehyde is used as a starting material.
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