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

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 sele...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-01, Vol.12 (3), p.432-437
Main Authors: Aursnes, M, Tungen, J E, Vik, A, Dalli, J, Hansen, T V
Format: Article
Language:English
Subjects:
Animals
Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis
Anti-Inflammatory Agents, Non-Steroidal - chemistry
Anti-Inflammatory Agents, Non-Steroidal - metabolism
Docosahexaenoic Acids - biosynthesis
Docosahexaenoic Acids - chemical synthesis
Docosahexaenoic Acids - chemistry
Lipids - chemistry
Mice
Molecular Structure
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob41902a