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 …