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Issue 3, 2014
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Stereoselective synthesis of protectin D1: a potent anti-inflammatory and proresolving lipid mediator

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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

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Supplementary files

Article information


Submitted
19 Sep 2013
Accepted
31 Oct 2013
First published
01 Nov 2013

This article is Open Access

Org. Biomol. Chem., 2014,12, 432-437
Article type
Paper

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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