Literature DB >> 27546916

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

Benzi I Estipona1, Beau P Pritchett1, Robert A Craig1, Brian M Stoltz1.   

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.

Entities:  

Keywords:  Allylic alkylation; Enantioselective; Eucomic acid; Palladium; Total synthesis

Year:  2016        PMID： 27546916      PMCID： PMC4986999          DOI： 10.1016/j.tet.2016.02.059

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  12 in total

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Authors:  Robert A Craig; Jennifer L Roizen; Russell C Smith; Amanda C Jones; Brian M Stoltz
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Authors:  Qi Liu; Eric M Ferreira; Brian M Stoltz
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9.  Catalytic enantioselective alkylation of substituted dioxanone enol ethers: ready access to Calpha-tetrasubstituted hydroxyketones, acids, and esters.

Authors:  Masaki Seto; Jennifer L Roizen; Brian M Stoltz
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  1 in total

Review 1.  The Allylic Alkylation of Ketone Enolates.

Authors:  Lukas Junk; Uli Kazmaier
Journal:  ChemistryOpen       Date:  2020-09-10       Impact factor: 2.630
  1 in total

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