Literature DB >> 25225129

Total synthesis of the anti-inflammatory and pro-resolving lipid mediator MaR1n-3 DPA utilizing an sp(3) -sp(3) Negishi cross-coupling reaction.

Jørn Eivind Tungen1, Marius Aursnes, Jesmond Dalli, Hildur Arnardottir, Charles Nicholas Serhan, Trond Vidar Hansen.   

Abstract

The first total synthesis of the lipid mediator MaR1n-3 DPA (5) has been achieved in 12 % overall yield over 11 steps. The stereoselective preparation of 5 was based on a Pd-catalyzed sp(3) -sp(3) Negishi cross-coupling reaction and a stereocontrolled Evans-Nagao acetate aldol reaction. LC-MS/MS results with synthetic material matched the biologically produced 5. This novel lipid mediator displayed potent pro-resolving properties stimulating macrophage efferocytosis of apoptotic neutrophils.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cross-coupling; inflammation; natural products; palladium; total synthesis

Mesh：

Substances：

Year:  2014        PMID： 25225129      PMCID： PMC4232850          DOI： 10.1002/chem.201404721

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  27 in total

1.  Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides.

Authors:  Forrest O Arp; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-08-03       Impact factor: 15.419

2.  Nickel-catalyzed Negishi cross-couplings of secondary nucleophiles with secondary propargylic electrophiles at room temperature.

Authors:  Sean W Smith; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  The first Negishi cross-coupling reaction of two alkyl centers utilizing a Pd-N-heterocyclic carbene (NHC) catalyst.

Authors:  Niloufar Hadei; Eric Assen B Kantchev; Christopher J O'Brien; Michael G Organ
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

4.  The docosatriene protectin D1 is produced by TH2 skewing and promotes human T cell apoptosis via lipid raft clustering.

Authors:  Amiram Ariel; Pin-Lan Li; Wei Wang; Wang-Xian Tang; Gabrielle Fredman; Song Hong; Katherine H Gotlinger; Charles N Serhan
Journal:  J Biol Chem       Date:  2005-10-10       Impact factor: 5.157

Review 5.  Resolvins and protectins in inflammation resolution.

Authors:  Charles N Serhan; Nicos A Petasis
Journal:  Chem Rev       Date:  2011-07-18       Impact factor: 60.622

6.  Room-temperature alkyl-alkyl Suzuki cross-coupling of alkyl bromides that possess beta hydrogens.

Authors:  M R Netherton; C Dai; K Neuschütz; G C Fu
Journal:  J Am Chem Soc       Date:  2001-10-17       Impact factor: 15.419

Review 7.  Pro-resolving lipid mediators are leads for resolution physiology.

Authors:  Charles N Serhan
Journal:  Nature       Date:  2014-06-05       Impact factor: 49.962

8.  A cyclopropanol-based strategy for subunit coupling: total synthesis of (+)-spirolaxine methyl ether.

Authors:  Katie A Keaton; Andrew J Phillips
Journal:  Org Lett       Date:  2007-06-09       Impact factor: 6.005

9.  Neuroprotectin D1: a docosahexaenoic acid-derived docosatriene protects human retinal pigment epithelial cells from oxidative stress.

Authors:  Pranab K Mukherjee; Victor L Marcheselli; Charles N Serhan; Nicolas G Bazan
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-19       Impact factor: 11.205

10.  Novel n-3 immunoresolvents: structures and actions.

Authors:  Jesmond Dalli; Romain A Colas; Charles N Serhan
Journal:  Sci Rep       Date:  2013       Impact factor: 4.379
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  17 in total

1.  Resolving Inflammation: Synthesis, Configurational Assignment, and Biological Evaluations of RvD1n-3 DPA.

Authors:  Jørn Eivind Tungen; Lisa Gerstmann; Anders Vik; Roberta De Matteis; Romain Alexandre Colas; Jesmond Dalli; Nan Chiang; Charles Nicholas Serhan; Markus Kalesse; Trond Vidar Hansen
Journal:  Chemistry       Date:  2018-12-20       Impact factor: 5.236

Review 2.  Transition metal-catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry.

Authors:  Junwon Choi; Gregory C Fu
Journal:  Science       Date:  2017-04-14       Impact factor: 47.728

Review 3.  Resolvins in inflammation: emergence of the pro-resolving superfamily of mediators.

Authors:  Charles N Serhan; Bruce D Levy
Journal:  J Clin Invest       Date:  2018-05-14       Impact factor: 14.808

4.  Synthesis of protectin D1 analogs: novel pro-resolution and radiotracer agents.

Authors:  J E Tungen; M Aursnes; S Ramon; R A Colas; C N Serhan; D E Olberg; S Nuruddin; F Willoch; T V Hansen
Journal:  Org Biomol Chem       Date:  2018-09-19       Impact factor: 3.876

5.  Synthesis of the 16S,17S-Epoxyprotectin Intermediate in the Biosynthesis of Protectins by Human Macrophages.

Authors:  Marius Aursnes; Jørn E Tungen; Romain A Colas; Iliyan Vlasakov; Jesmond Dalli; Charles N Serhan; Trond V Hansen
Journal:  J Nat Prod       Date:  2015-11-18       Impact factor: 4.050

6.  Synthesis of 13(R)-Hydroxy-7Z,10Z,13R,14E,16Z,19Z Docosapentaenoic Acid (13R-HDPA) and Its Biosynthetic Conversion to the 13-Series Resolvins.

Authors:  Karoline G Primdahl; Marius Aursnes; Mary E Walker; Romain A Colas; Charles N Serhan; Jesmond Dalli; Trond V Hansen; Anders Vik
Journal:  J Nat Prod       Date:  2016-10-05       Impact factor: 4.050

Review 7.  Interplay Between n-3 and n-6 Long-Chain Polyunsaturated Fatty Acids and the Endocannabinoid System in Brain Protection and Repair.

Authors:  Simon C Dyall
Journal:  Lipids       Date:  2017-09-05       Impact factor: 1.880

Review 8.  Mediterranean Diet: Lipids, Inflammation, and Malaria Infection.

Authors:  Adriana R Silva; Bianca P T Moraes; Cassiano F Gonçalves-de-Albuquerque
Journal:  Int J Mol Sci       Date:  2020-06-24       Impact factor: 5.923

9.  A new synthetic protectin D1 analog 3-oxa-PD1n-3 DPA reduces neuropathic pain and chronic itch in mice.

Authors:  Jannicke Irina Nesman; Ouyang Chen; Xin Luo; Ru-Rong Ji; Charles N Serhan; Trond Vidar Hansen
Journal:  Org Biomol Chem       Date:  2021-03-09       Impact factor: 3.876

Review 10.  Long-chain omega-3 fatty acids and the brain: a review of the independent and shared effects of EPA, DPA and DHA.

Authors:  Simon C Dyall
Journal:  Front Aging Neurosci       Date:  2015-04-21       Impact factor: 5.750
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