Sharpless Epoxidation - Synthetic Utility

Synthetic Utility

The Sharpless Epoxidation is viable with a large range of primary and secondary olefinic alcohols. Furthermore, with the exception noted above, a given dialkyl tartrate will preferentially add to the same face independent of the substitution on the olefin. To demonstrate the synthetic utility of the Sharpless Epoxidation, the Sharpless group created synthetic intermediates of various natural products: methymycin, erythromycin, leukotriene C-1, and (+)-disparlure.

As one of the few, highly enantioselective reactions during its time, many manipulations of the of the 2,3-epoxyalcohols have been developed.

The Sharpless Epoxidation has been used for the total synthesis of various carbohydrates, terpenes, leukotrienes, pheromones, and antibiotics.

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