First total synthesis of 4(R),17(R)-Resolvin D6 stereoisomer, a potent neuroprotective docosanoid

[Display omitted] The first total synthesis of a novel neuroprotective Resolvin D6 enantiomer, 4(R),17(R)-Resolvin D6, is described. Resolvin D6 is a lipid mediator derived from docosahexaenoic acid (DHA, C22:6, ω-3) with anti-inflammatory properties. Key synthetic features include the use of a MacM...

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Bibliographic Details
Published in:Tetrahedron letters 2022-09, Vol.106, p.154091, Article 154091
Main Authors: Nshimiyimana, Robert, Fung Lam, Ting, Aggarwal, Shubhangi, G. Bazan, Nicolas, Bazan, Haydee E.P., Petasis, Nicos A.
Format: Article
Language:English
Subjects:
Anti-inflammatory properties
Asymmetric organocatalysis
Resolvin D6
Stereoisomer
Total synthesis
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Summary:[Display omitted] The first total synthesis of a novel neuroprotective Resolvin D6 enantiomer, 4(R),17(R)-Resolvin D6, is described. Resolvin D6 is a lipid mediator derived from docosahexaenoic acid (DHA, C22:6, ω-3) with anti-inflammatory properties. Key synthetic features include the use of a MacMillan enantioselective organocatalytic α-oxidation of aldehydes in conjunction with a chiral pool-based approach to generate chiral synthons, a 1,4‑enyne unit as a linchpin, as well as a (Z)-selective Wittig coupling to assemble the Resolvin D6 core carbon skeleton.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.154091