Journal
TETRAHEDRON LETTERS
Volume 56, Issue 14, Pages 1843-1846Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.02.080
Keywords
Maresin 1; Lipid mediator; Stereoselective synthesis; Nagao-Evans aldol; Pro-resolution
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Funding
- School of Pharmacy, University of Oslo
- Norwegian Research Council (KOSK II)
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Maresin 1 is a potent anti-inflammatory and pro-resolving lipid mediator derived from docosahexaenoic acid. The total synthesis of maresin 1 is achieved in 10 steps and in 7% overall yield. The Evans Nagao aldol reaction between (2E,4E)-5-bromopenta-2,4-dienal and different chiral auxiliaries is investigated. The reported synthesis is efficient and highly stereoselective, affording multi-milligram quantities of this biologically interesting lipid mediator. (C) 2015 Elsevier Ltd. All rights reserved.
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