The pyrrole approach toward the synthesis of fully functionalized cup-shaped molecules.

[reaction: see text] A novel method for the synthesis of new highly functionalized cyclotrimers is described. The method consists of an original synthesis of beta-dibromosubstituted pyrroles, metalation, cycloaddition, and cyclotrimerization. The sequence is highly compatible with common functional groups and allows the construction of cup-shaped molecules functionalized both at the upper and bottom rim. This feature makes the newly formed structures useful scaffolds for the development of supramolecular receptors.