Efficient synthesis of novel macrocyclic tetraamide compounds: a unique reaction process involving both self-assembling and folding of intermediates

A macrocycle having two isobutenyl and four amide moieties was successfully formed via two kinds of acyclic intermediates. These key intermediates possess the ability to self-organize due to intra- or intermolecular hydrogen-bonding interactions. In both intermediates, preorganized structures were favorably subject to nucleophilic attack at the carbonyl group by a terminal amino group, and preorganization made it possible to form the macrocycle under mild conditions.