249934-93-8

Upstream product

• 249935-24-8 (E)-(R)-7-[(1S,2R,3R,5S)-3-Acetoxy-5-hydroxy-2-((Z)-oct-2-enyl)-cyclopentyl]-5-hydroxy-hept-6-enoic acid ethyl ester 
• 1025719-78-1 methyl (R,E)-7-{(1S,2R,3R,5S)-3,5-bis(tert-butyldimethylsilyloxy)-2-[(Z)-oct-2-enyl]cyclopentyl}-5-(tert-butyldimethylsilyloxy)hept-6-enoate 
• 249935-23-7 (E)-7-[(1S,2R,3R,5S)-3-Acetoxy-5-hydroxy-2-((Z)-oct-2-enyl)-cyclopentyl]-5-oxo-hept-6-enoic acid ethyl ester 
• 377078-52-9 C₄₂H₇₂O₃Si₃ 
• 377078-54-1 C₄₄H₅₂O₅Si 
• 377078-57-4 C₃₅H₄₂O₇ 
• 377078-53-0 (1R,3S,4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((Z)-oct-2-enyl)-cyclopentane-1,3-diol 
• 377078-55-2 C₂₈H₃₄O₅ 
• 377078-56-3 C₂₈H₃₂O₅ 
• 213777-18-5 (1S,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane 
• 213777-19-6 (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol 
• 377078-59-6 C₃₅H₄₄O₇ 

Relevant academic research and scientific papers

A cross-metathesis route to the 5-F2-isoprostanes

(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.

Syntheses and preliminary pharmacological evaluation of the two epimers of the 5-F2t-isoprostane

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.

5-F2t-isoprostane, a human hormone?

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