Issue 19, 2022

First stereoselective total synthesis of 4(S),5(S)-oxido-17(S)-hydroxy-6(E),8(E),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid, the biosynthetic precursor of resolvins D3 and D4

Abstract

The first total convergent synthesis of 4(S),5(S)-oxido-17(S)-hydroxy-6(E),8(E),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid (1) is described. The reported synthesis led to confirmation of the native epoxydocosahexaenoic acid as the biosynthetic precursor of lipid mediators resolvin D3 and resolvin D4. These potent enzymatic products of docosahexaenoic acid (DHA) are important signaling molecules in the resolution of inflammation. A stereocontrolled and chiral pool-based synthetic strategy was employed, with key features including epoxide transposition under basic conditions to form the oxirane ring, and a cis-selective Wittig reaction to secure the target docosahexaenoate backbone.

Graphical abstract: First stereoselective total synthesis of 4(S),5(S)-oxido-17(S)-hydroxy-6(E),8(E),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid, the biosynthetic precursor of resolvins D3 and D4

Supplementary files

Article information

Article type
Paper
Submitted
08 Mar 2022
Accepted
19 Mar 2022
First published
19 Apr 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 11613-11618

First stereoselective total synthesis of 4(S),5(S)-oxido-17(S)-hydroxy-6(E),8(E),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid, the biosynthetic precursor of resolvins D3 and D4

R. Nshimiyimana, T. F. Lam, S. Aggarwal, C. N. Serhan and N. A. Petasis, RSC Adv., 2022, 12, 11613 DOI: 10.1039/D2RA01537D

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