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

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journal contribution
posted on 28.11.2000, 00:00 authored by Peter Wipf, Joey-Lee Methot
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.