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Literature DB >> 31379396

Synthesis of an Electrophilic Keto-Tetraene 15-oxo-Lipoxin A₄ Methyl Ester via a MIDA Boronate.

Steven R Woodcock¹, Stacy G Wendell¹, Francisco J Schopfer¹, Bruce A Freeman¹.

Abstract

15-oxo-Lipoxin A4 (15-oxo- LXA4) has been identified as a natural metabolite of the fatty acid signaling mediator Lipoxin A4. Herein, we report a total synthesis of the methyl ester of 15-oxo-LXA4 to be used in investigations of potential electrophilic bioactivity of this metabolite. The methyl ester of 15-oxo-LXA4 was synthesized in a convergent 15 step (9 steps longest linear) sequence starting from 1-octyn-3-ol and 2-deoxy-D-ribose with Sonogashira and Suzuki cross-couplings of a MIDA boronate as key steps.

Entities: Chemical

Keywords: MIDA boronate; eicosanoid; electrophile; palladium-catalyzed coupling

Year: 2018 PMID： 31379396 PMCID： PMC6677397 DOI： 10.1016/j.tetlet.2018.08.014

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

27 in total

1. Oxidoreductases in lipoxin A4 metabolic inactivation: a novel role for 15-onoprostaglandin 13-reductase/leukotriene B4 12-hydroxydehydrogenase in inflammation.

Authors: C B Clish; B D Levy; N Chiang; H H Tai; C N Serhan
Journal: J Biol Chem Date: 2000-08-18 Impact factor: 5.157

2. Simple, efficient, and modular syntheses of polyene natural products via iterative cross-coupling.

Authors: Suk Joong Lee; Kaitlyn C Gray; James S Paek; Martin D Burke
Journal: J Am Chem Soc Date: 2008-01-16 Impact factor: 15.419

3. A simple and modular strategy for small molecule synthesis: iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks.

Authors: Eric P Gillis; Martin D Burke
Journal: J Am Chem Soc Date: 2007-05-09 Impact factor: 15.419

4. Cyclooxygenase-2 generates anti-inflammatory mediators from omega-3 fatty acids.

Authors: Alison L Groeger; Chiara Cipollina; Marsha P Cole; Steven R Woodcock; Gustavo Bonacci; Tanja K Rudolph; Volker Rudolph; Bruce A Freeman; Francisco J Schopfer
Journal: Nat Chem Biol Date: 2010-05-02 Impact factor: 15.040

Review 5. Lipoxins and aspirin-triggered 15-epi-lipoxins are the first lipid mediators of endogenous anti-inflammation and resolution.

Authors: Charles N Serhan
Journal: Prostaglandins Leukot Essent Fatty Acids Date: 2005 Sep-Oct Impact factor: 4.006

Review 6. Lipoxins: regulators of resolution.

Authors: Aidan Ryan; Catherine Godson
Journal: Curr Opin Pharmacol Date: 2010-03-11 Impact factor: 5.547

7. 15-oxo-Eicosatetraenoic acid, a metabolite of macrophage 15-hydroxyprostaglandin dehydrogenase that inhibits endothelial cell proliferation.

Authors: Cong Wei; Peijuan Zhu; Sumit J Shah; Ian A Blair
Journal: Mol Pharmacol Date: 2009-06-17 Impact factor: 4.436

8. Novel 3-oxa lipoxin A4 analogues with enhanced chemical and metabolic stability have anti-inflammatory activity in vivo.

Authors: William J Guilford; John G Bauman; Werner Skuballa; Shawn Bauer; Guo Ping Wei; David Davey; Caralee Schaefer; Cornell Mallari; Jennifer Terkelsen; Jih-Lie Tseng; Jun Shen; Babu Subramanyam; Arndt J Schottelius; John F Parkinson
Journal: J Med Chem Date: 2004-04-08 Impact factor: 7.446

9. Cyclooxygenase-2-mediated metabolism of arachidonic acid to 15-oxo-eicosatetraenoic acid by rat intestinal epithelial cells.

Authors: Seon Hwa Lee; Kannan Rangiah; Michelle V Williams; Angela Y Wehr; Raymond N DuBois; Ian A Blair
Journal: Chem Res Toxicol Date: 2007-10-02 Impact factor: 3.739