Practical Synthesis of a Highly Enantioselective Receptor for Peptides

Article abstract of DOI:10.1021/jo00058a005

A practical synthesis of a highly enantioselective, C₃-symmetric host molecule (2) has been developed.The basic strategy is a significant improvement over the relatively lenghty previous synthesis and involves direct addition of a Boc-tyrosine amide anion derivative 4 to methyl 3,5-bis(bromomethyl)benzoate to give an advanced intermediate (5).The final step, a triple macrolactamization, closes three 19-membered rings simultaneously to produce the bridged macrotricyclic receptor in 70-80percent yield.