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A library of isopulegol-based β -amino acid derivatives has been developed from commercially-available (-)-isopulegol. Michael addition of primary and secondary amines towards α , β -unsaturated γ -lactones was accomplished resulting in β -aminolactones in highly-stereoselective reactions. Ring-opening of β -aminolactones with different amines furnished excellent yields of β -aminoamides. Moreover, the applicability of aminolactones in peptide synthesis was examined by opening the lactone ring with α - and β -aminoesters, providing dipeptides as promising chiral substrates for the synthesis of foldamers. The antiproliferative activities of β -aminolactones and β -aminoamides were explored, and the structure-activity relationships were studied from the aspects of the stereochemistry of the monoterpene ring and the substituent effects on the β -aminoamide ring system. The N -unsubstituted (-)-isopulegol-based β -aminoamides exhibited considerable antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, MCF7 and MDA-MB-231).

Synthesis and Transformation of (-)-Isopulegol-Based Chiral β-Aminolactones and β-Aminoamides