Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 3, Pages 432-437Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob41902a
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Funding
- Norwegian Research Council (KOSK II)
- School of Pharmacy, University of Oslo
- Norwegian Research Council
- National Institutes of Health GM Grant [PO1GM095467]
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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.
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