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Fixed on an aromatic platform in a conformationally defined way, acyclic (E)-alkenes can be considered gripped on a molecular workbench. The olefinic ansa-macrolides formed in this way are shielded on one face. On epoxidation and dihydroxylation [Eq. (1)] the attack on the double bond takes place diastereoselectively from outside the ring, and the ansa chain can subsequently be cleaved from the workbench by mild hydrogenolysis. Bn=benzyl, NMO=N-methylmorpholin-N-oxide.
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Mulzer et al. (1998) studied this question.
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