Issue 3, 2014

Stereoselective synthesis of protectin D1: a potent anti-inflammatory and proresolving lipid mediator

Abstract

A convergent stereoselective synthesis of the potent anti-inflammatory, proresolving and neuroprotective lipid mediator protectin D1 (2) has been achieved in 15% yield over eight steps. The key features were a stereocontrolled Evans-aldol reaction with Nagao's chiral auxiliary and a highly selective Lindlar reduction of internal alkyne 23, allowing the sensitive conjugated E,E,Z-triene to be introduced late in the preparation of 2. The UV and LC/MS–MS data of synthetic protectin D1 (2) matched those obtained from endogenously produced material.

Graphical abstract: Stereoselective synthesis of protectin D1: a potent anti-inflammatory and proresolving lipid mediator

Supplementary files

Article information

Article type
Paper
Submitted
19 Sep 2013
Accepted
31 Oct 2013
First published
01 Nov 2013
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2014,12, 432-437

Stereoselective synthesis of protectin D1: a potent anti-inflammatory and proresolving lipid mediator

M. Aursnes, J. E. Tungen, A. Vik, J. Dalli and T. V. Hansen, Org. Biomol. Chem., 2014, 12, 432 DOI: 10.1039/C3OB41902A

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