A solid-phase approach towards the development of 3-aza-6,8-dioxabicyclo[3.2.1]octane scaffolds

The development of new strategies for solid-phase synthesis of 3-aza-6,8-dioxabicyclo3.2.1]octane scaffolds, named BTKa, is described. The preparation was made possible by the combination of three components: amines, alpha-halo-acetophenones, and sugar or tartaric acid derivatives. By anchoring each of the three components it was possible to synthesize BTKa compounds either as amino alcohols or amido esters. The compatibility of the protocols with different classes of amines and substituted alpha-halo-acetophenones was demonstrated.