Asymmetric synthesis and conformational analysis of the two enantiomers of the saturated analog of the potent thrombin inhibitor MOL-376

Asymmetric synthesis of the two enantiomers of a small molecule thrombin inhibitor is described. The key step in the synthesis is the glucose-directed chiral induction in the hetero Diels–Alder cycloaddition step. Conformational analysis indicates that the S-enantiomer is a better fit for the idealized β-strand conformation.