Stereoselective synthesis of two highly potent 5-oxo-ETE receptor antagonists

[Display omitted] Enantioselective synthesis of highly potent 5-oxo-ETE receptor antagonists 5a and 6a with a high level of enantiomeric purity is described. The main feature of this work is the simple and efficient synthesis of the bi-functionalized 3-(S)-methyl-pentanedioic acid monomethyl ester (...

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Bibliographic Details
Published in:Tetrahedron letters 2015-12, Vol.56 (49), p.6896-6899
Main Authors: Nagendra Reddy, Chintam, Ye, Qiuji, Chourey, Shishir, Gravel, Sylvie, Powell, William S., Rokach, Joshua
Format: Article
Language:English
Subjects:
(S)-Tol-BINAP
5-Oxo-ETE
Conjugate addition
Eosinophils
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Summary:[Display omitted] Enantioselective synthesis of highly potent 5-oxo-ETE receptor antagonists 5a and 6a with a high level of enantiomeric purity is described. The main feature of this work is the simple and efficient synthesis of the bi-functionalized 3-(S)-methyl-pentanedioic acid monomethyl ester (24) with the enantiomeric ratio of S/R:98.4/1.6. We investigated the asymmetric conjugate addition of MeMgBr to 5-Benzyloxy-pent-2-enoic acid methyl ester (23) catalyzed by the CuBr/(S)-Tol-BINAP system, and optimized the reaction conditions toward regioselectivity and high enantioselectivity.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.10.097