Total Synthesis of 4(R),17(R)-Resolvin D6 Stereoisomer, a Potent Neuroprotective Docosanoid

Authors

• Robert Nshimiyimana, University of Southern California, Los Angeles, CA
• Ting Fung Lam, University of Southern California, Los Angeles, CA
• Nicolas G. Bazan, LSU Health Sciences Center - New OrleansFollow
• Haydee E. Bazan, LSU Health Sciences Center - New OrleansFollow
• Nicos A. Petasis, University of Southern California, Los Angeles, CA

Document Type

Article

Publication Date

9-14-2022

Publication Title

SSRN Electronic Journal

Abstract

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.

First Page

1

Last Page

6

Volume

14

Publisher

Elsevier

Rights

© 2022 Elsevier Ltd. All rights reserved.

Recommended Citation

Nshimiyimana, Robert; Lam, Ting Fung; Bazan, Nicolas G.; Bazan, Haydee E.; and Petasis, Nicos A., "Total Synthesis of 4(R),17(R)-Resolvin D6 Stereoisomer, a Potent Neuroprotective Docosanoid" (2022). School of Medicine Faculty Publications. 4515.
https://digitalscholar.lsuhsc.edu/som_facpubs/4515
10.1016/j.tetlet.2022.154091