- A cross-metathesis route to the 5-F2-isoprostanes
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(Chemical Equation Presented) A library of eight 5-F2- isoprostanes was prepared through a ring-opening metathesis/cross-metathesis protocol between functionalized bicyclo[3.2.0]heptenes, ethylene, and α,β-unsaturated ketones. This sequence provided racemic enones in a regio- and stereoselective fashion that could be converted to enantiomerically enriched allylic alcohols through a catalyst-controlled asymmetric reduction. Completion of the sidechains, followed by global deprotection, resulted in a stereodivergent route to eight enantiomerically enriched 5-F2 isoprostanes. Overall, the synthesis of this library of known and anticipated lipid oxidation metabolites was achieved in 10 steps from commercially available 4-hydroxy-2-cyclopentenone.
- Pandya, Bhaumik A.,Snapper, Marc L.
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p. 3754 - 3758
(2008/09/20)
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- Syntheses and preliminary pharmacological evaluation of the two epimers of the 5-F2t-isoprostane
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The total synthesis of the 5-F2t-isoprostane 1 and its 5-epimer 2 from diacetone-D-glucose is described. We report preliminary data on the vascular properties of these compounds.
- Durand, Thierry,Cracowski, Jean-Luc,Guy, Alexandre,Rossi, Jean-Claude
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p. 2495 - 2498
(2007/10/03)
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- 5-F2t-isoprostane, a human hormone?
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Syntheses of the four enantiomerically pure diastereomers of 5-F2t-isoprostane (5-8) are described. The key step is the lipase-catalyzed chemo-enzymatic resolution of the racemic diol 40 to give the mono-acetates 41 and 42. The enantiomerically
- Taber, Douglass F.,Kanai, Kazuo,Pina, Richard
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p. 7773 - 7777
(2007/10/03)
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- Total synthesis of a novel isoprostane IPF(2α)-I and its identification in biological fluids
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The first tokai synthesis of IPF(2α)-I 25 is described using D-glucose as starting material. This novel isoprostane has been used to establish its presence in human urine.
- Adiyaman, Mustafa,Lawson, John A.,Hwang, Seong-Woo,Khanapure, Subhash P.,FitzGerald, Garret A.,Rokach, Joshua
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p. 4849 - 4852
(2007/10/03)
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