Synthetic studies on bryostatins, potent antineoplastic agents: Synthesis of the C17-C27 fragment of C20 oxygenated bryostatins

Article abstract of DOI:10.1016/0040-4039(95)01310-E

Synthetic process towards the bottom half portion of C₂₀ oxygenated series of bryostatins is described. The stereogenic center at C₂₀ position was constructed through a hydroxyl group-directed epoxidation by using mCPBA. It was found that silver (I) salt is an effective and mild reagent for regioselective ring cleavage of α-bromoepoxides into the corresponding α-hydroxyketones via oxonium ion intermediates.