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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 ?-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.

SUBMITTER: Estipona BI 

PROVIDER: S-EPMC4986999 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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Catalytic enantioselective total synthesis of (+)-eucomic acid.

Estipona Benzi I BI   Pritchett Beau P BP   Craig Robert A RA   Stoltz Brian M BM  

Tetrahedron 20160302 26

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. ...[more]

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