scholarly journals Changes in eicosapentaenoic acid and docosahexaenoic acid and risk of cardiovascular events and atrial fibrillation: A secondary analysis of the OMEMI trial

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pp. 978-983 ◽  
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Kim A. Connelly ◽  
Howard Leong-Poi ◽  
Xudong Hu ◽  
Hiroko Fujii ◽  
...  

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pp. 1453
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Viet T. Le ◽  
Stacey Knight ◽  
Kirk Knowlton ◽  
Raymond McCubrey ◽  
Jeramie D. Watrous ◽  
...  

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Vol 41 (1) ◽  
pp. 23-27 ◽  
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E. Molina Grima ◽  
J. A. S�nchez P�rez ◽  
F. Garc�a Camacho ◽  
J. M. Fern�ndez Sevilla ◽  
F. G. Aci�n Fern�ndez

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2019 ◽  
Vol 30 (03) ◽  
pp. 338-342
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Shun Saito ◽  
Yuichi Kobayashi

Wittig reactions using carboxy (CO2H) ylides derived from a carboxylic phosphonium salt and NaN(TMS)2 (NaHMDS) in a 1:1 ratio were applied to the synthesis of 8-HEPE and 10-HDoHE, which are metabolites of eicosapentaenoic acid and docosahexaenoic acid, respectively. The attempted Wittig reaction of 3-(TBS-oxy)pentadeca-4E,6Z,9Z,12Z-tetraenal with the carboxy ylide (2 equiv) derived from Br– Ph3P+(CH2)4CO2H and NaHMDS (1:1) competed with the elimination of the TBS-oxy group at C3 to give a mixture of the Wittig product and the elimination product in 45–50% and 30–40% yields, respectively. The elimination was suppressed completely by using three equiv of the carboxy ylides in THF/HMPA (7–8:1), and the subsequent desilylation gave 8-HEPE in (R)- and (S)-forms. Similarly, both enantiomers of 10-HDoHE were synthesized.


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