title: Catalytic enantioselective total synthesis of (+)-eucomic acid.
abstract: A catalytic enantioselective synthesis of (+)-eucomic acid is reported. A palladium-catalyzed asymmetric allylic alkylation is employed to access the chiral tetrasubstituted α-hydroxyacid moiety found in the natural product. The protecting group strategy was investigated, and a protecting group manipulation was made without any appreciable deleterious effects in the allylic alkylation reaction. Non-natural (+)-eucomic acid is synthesized in a longest linear sequence of 13 steps.
authors.affiliation: Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd MC 101-20, Pasadena, CA 91125, United States of America.
authors.forename: Benzi I
authors.initials: BI
authors.lastname: Estipona
authors.affiliation: Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd MC 101-20, Pasadena, CA 91125, United States of America.
authors.forename: Beau P
authors.initials: BP
authors.lastname: Pritchett
authors.affiliation: Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd MC 101-20, Pasadena, CA 91125, United States of America.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Craig
authors.affiliation: Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E California Blvd MC 101-20, Pasadena, CA 91125, United States of America.
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
keywords: Allylic alkylation; Enantioselective; Eucomic acid; Palladium; Total synthesis