Template-directed synthesis of shape-persistent macrocyclic amphiphiles with convergently arranged functionalities

The template-directed synthesis of shape-persistent macrocyclic amphiphiles is described. Two macrocycles with convergently arranged functional groups (hydroxyl and carboxylic acids) are prepared by intramolecular Glaser coup ling of the appropriate templated tetraacetylenes. These structures are for med by thr: quadruple Hagihara coupling of monoprotected bisacetylenes to a ppropriate tetraiodides and subsequent desilylation, resulting in a rapid i ncrease of complexity of the intermediates as well as easy formation of str uctures with different convergent functional groups.