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

M Aursnes, JE Tungen, A Vik, J Dalli… - Organic & biomolecular …, 2014 - pubs.rsc.org
M Aursnes, JE Tungen, A Vik, J Dalli, TV Hansen
Organic & biomolecular chemistry, 2014pubs.rsc.org
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 …
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.
The Royal Society of Chemistry
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