67529-24-2

Upstream product

• 65844-23-7 (+/-)-(5S)-mesyloxy-(6R)-prostaglandin I₁ methyl ester 
• 65844-23-7 (S)-5-[(2S,3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-5-methanesulfonyloxy-pentanoic acid methyl ester 
• 65844-23-7 (+/-)-(5R)-mesyloxy-(6S)-prostaglandin I₁ methyl ester 
• 65844-23-7 (R)-5-[(2R,3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-5-methanesulfonyloxy-pentanoic acid methyl ester 

Downstream Products

• 71425-68-8 γ-(6R,9α,11α,13E,15S)-6,9-epoxy-4,11,15-trihydroxy-5-(phenylseleno)-prosta-13-en-1-oic acid lactone 

Relevant academic research and scientific papers

Synthesis of (+/-)-Prostaglandin I2 Methyl Ester and its 15-Epimer from 2-(Cyclopent-2-enyl)-1-(2-oxocyclopentyl)ethanol Derivatives

The threo-2-(cyclopent-2-enyl)-1-(2-oxocyclopentyl)ethanol derivatives (2) and (3) have been converted into (+/-)-prostaglandin I2 methyl ester and its 15-epimer.The route involved halogenoetherification, hydrodehalogenation, Baeyer-Villiger oxidation, and methanolysis, to give the 5-hydroxyprostaglandin I1 derivatives (17) and (18).These hydroxy esters were mesylated, the 11- and 15-hydroxy groups were deprotected, and the resulting 15-epimeric alcohols were separated.The final elimination, accomplished by means of neat 1,8-diazabicycloundec-7-ene, gave the required Δ5-olefin with a high degree of regioselectivity, and was stereospecifically trans, giving the required Z-configuration (25).