Synthesis of the PMB ether of 5,6-epoxyisoprostane E2 through aldol reaction of the α-bromocyclopentanone.
5,6-Epoxyisoprostane E2 was synthesized via bromohydrination of the cyclopentene and aldol reaction of the α-bromocyclopentanone with the epoxyaldehyde. High regioselectivity in the bromohydrination was attained with recrystallized NBS and pyridine in aqueous DMSO. The enolate for the aldol reaction was generated by adding t-BuLi to the mixture of the α-bromocyclopentanone and ZnI2. This aldol protocol was applied successfully to several cyclopentanones and aldehydes.
Department of Bioengineering, Tokyo Institute of Technology , Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan.
Hidehisa
H
Kawashima
Yuichi
Y
Kobayashi
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D028421:Isoprostanes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
C000589437:5,6-epoxyisoprostane E2; D000447:Aldehydes; D003517:Cyclopentanes; D004987:Ethers; D006842:Hydrocarbons, Brominated; D028421:Isoprostanes; C007201:cyclopentanone; C116609:3-hydroxybutanal