Total Synthesis and Stereochemical Revision of (+)-Aeruginosin 298-A

Novel routes toward both enantiomers of the bicyclic proline surrogate 2-carboxy-6-hydroxyoctahydroindole, i.e., Choi, were developed on the basis of the oxidative cyclization of l-tyrosine. Synthesis of the proposed sequence of (+)-aeruginosin 298-A did not provide the natural product. Incorporation of a d-leucine residue, in contrast, led to the total synthesis of this thrombin inhibitor.