Catalytic enantioselective total synthesis of (+)-eucomic acid

TETRAHEDRON

卷:72

Article

Estipona, Benzi I.¹  Pritchett, Beau P.¹  Craig, Robert A., II¹  Stoltz, Brian M.¹ 

[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, 1200 E Calif Blvd,MC 101-20, Pasadena, CA 91125 USA

关键词: Allylic alkylation;    Enantioselective;    Eucomic acid;    Palladium;    Total synthesis;   

DOI  :  10.1016/j.tet.2016.02.059

来源: Elsevier

【 摘 要 】

A catalytic enantioselective synthesis of (+)-eucomic acid is reported. A palladium-catalyzed asymmetric allylic alkylation is employed to access the chiral tetrasubstituted alpha-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. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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