180469-63-0Relevant articles and documents
A cross-metathesis route to the 5-F2-isoprostanes
Pandya, Bhaumik A.,Snapper, Marc L.
, p. 3754 - 3758 (2008/09/20)
(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.
5-F2t-isoprostane, a human hormone?
Taber, Douglass F.,Kanai, Kazuo,Pina, Richard
, p. 7773 - 7777 (2007/10/03)
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