On the reactivity of ascomycin at the binding domain. Part 2: Hydroxide mediated rearrangement reactions

The natural product ascomycin represents a highly functionalised 23-membered macrocycle with a polyketide backbone. Within the binding domain, ascomycin features the unusual pattern of a masked tricarbonyl moiety, which potentially allows for high structural diversity via simple isomerisation events. Herein, highly stereoselective, hydroxide mediated rearrangement reactions at the binding domain are reported.