A seven-step synthesis starting from 1 furnished the dienediyne analog 2 of the pharmacophore 3 of the antitumor agent neocarzinostatin. The eleven-membered ring of 2 was formed by the McMurry cyclization of a ketoaldehyde precursor. The resulting C = C bond was epoxidized selectively by taking advantage of a combination of substrate and reagent control. Tf = CF3SO2, Ar = aryl.
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Eckhardt et al. (1996) studied this question.
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