98497-17-7

Upstream product

• 98574-71-1 S,S-(+)-methyl <7-(5-hydroxy-2-oxo-3-cyclopentenyl)>-5(Z)-heptenoate 
• 98574-68-6 (Z)-7-((1R,2R,3R,5S)-3-Hydroxy-6-oxa-bicyclo[3.1.0]hex-2-yl)-hept-5-enoic acid 
• 98574-70-0 (+)-methyl <7-(2,3-β-epoxy-5-oxo-cyclopent-β-yl)>-5(Z)-heptenoate 
• 98574-69-7 (Z)-7-((1R,2R,3R,5S)-3-Hydroxy-6-oxa-bicyclo[3.1.0]hex-2-yl)-hept-5-enoic acid methyl ester 
• 54556-18-2 S-(-)-methyl <7-(3-hydroxy-5-oxo-1-cyclopentenyl)>-5(Z)-heptenoate 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Relevant academic research and scientific papers

Total synthesis of E1 and E2 isoprostanes by diastereoselective protonation

A short total synthesis of the E-type isoprostanes has been achieved using a two-component coupling process combined with a diastereoselective protonation under reagent control. Mild cleavage of the silyl protective groups with cat. BiBr3 or HF/Py followed by enzymatic hydrolysis of the methyl ester afforded the free E-type isoprostanes.

Novel molecular rearrangements of 4-hydroxy-2-cyclopentenones

Novel rearrangements of hydroxycyclopentenone derivatives 1 and 24 to 7,9,11 and 31,33,35 are reported. The stereochemistry of the rearrangement is interpreted as the result of synchronous enolate induced [1.5]-sigmatropic rearrangement and stepwise addition-elimination process. Preparation of the various substrates and structural elucidation of new products are also described.