Total synthesis and stereochemical revision of (+)-aeruginosin 298-A.
[structure:see text] 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.
Wipf
P
P
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. pwipf+@pitt.edu
Methot
J L
JL
D000991:Antithrombins / Q000138:chemical synthesis* / Q000737:chemistry; D007930:Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000991:Antithrombins; C419325:aeruginosin 298-A; D007930:Leucine