98818-31-6

Basic information

• Product Name: 3-Cyclopentene-1-heptanoic acid, 2-hydroxy-5-oxo-, methyl ester
• CAS NO: 98818-31-6
• Molecular Formula: C13H20O4
• Molecular Weight: 240.299
• Mol File: 98818-31-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-Cyclopentene-1-heptanoic acid, 2-hydroxy-5-oxo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclopentene-1-heptanoic acid, 2-hydroxy-5-oxo-, methyl ester(98818-31-6)
• EPA Substance Registry System: 3-Cyclopentene-1-heptanoic acid, 2-hydroxy-5-oxo-, methyl ester(98818-31-6)

Safety Data

• Hazardous Substances Data: 98818-31-6(Hazardous Substances Data)

Upstream product

• 98736-11-9 9-((1S,2R,3S)-2,3-Dimethoxy-cyclopropyl)-9-oxo-nonanoic acid methyl ester 
• 101650-79-7 methyl 8-(2-furyl)-8-hydroxy-octanoate 

Downstream Products

• 41138-61-8 (4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone 
• 40098-26-8 methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate 

Relevant articles and documents

An efficient asymmetric synthesis of prostaglandin E1

An asymmetric total synthesis of Prostaglandin E1 (5) has been achieved in a two-component coupling process. The chiral hydroxycyclopentenone 6 was readily available from furan with 96% ee. The key reaction step was a kinetic enzymatic resolution followed by an in situ inversion. A catalytic asymmetric reduction of the γ-iodo vinyl ketone 19 with the Corey CBS catalyst gave the ω-side chain 7 with >96% ee. Conjugate addition using the reaction with dilithiocyanocuprate followed by mild cleavage of the silyl protective groups and enzymatic hydrolysis of the methyl ester 22 gave (-)-PGE1 5 in high yield.

Oxocyclopentenol Syntheses

Metal-assisted decomposition of α-diazo carbonyl compounds in 1,2-dialkoxy-1-alkenes are shown to yield β,β'-dialkoxycyclopropyl carbonyl systems, whose acid hydrolysis produces α-alkoxy-γ-dicarbonyl substances.Intramolecular condensations of the latter lead to oxocyclopentenols.Application of this reaction scheme to the syntheses of a prostaglandin intermediate and of tetrahydropyrethrolone is described.