Divergent synthetic routes to biologically relevant types of compounds: Chiral polyfunctional γ-lactams and amino acids

© 2014 Elsevier Ltd. Divergent and versatile synthetic routes leading to the title compounds are described. They start from a common chiral precursor derived from (-)-(S)-verbenone and afford polyfunctional γ-lactams and γ- and ε-amino acids. The cyclobutane moiety in these molecules acts as a chiral and polyfunctional platform providing stereogenic centres with unambiguous absolute configuration that control the chirality of the newly produced asymmetric carbons. Furthermore, it affords functional groups and carbon chains suitable not only to create the basic skeleton of the desired products but additional functional groups. These features confer on these derivatives a great versatility for further uses in the development of new drugs and as synthetic building blocks.