engleski

Synthesis and enantioseparation of (±)-halogenated marinoaziridine derivatives

Marinoaziridines A and B are the first aziridine- containing natural products isolated from Gram- negative bacteria from marine sediment.1 Their absolute configuration is so far unknown as well as their total synthesis. Many aziridine- containing compounds demonstrate very useful pharmacological activity including anticancer, antibacterial, antimicrobial activity, etc. strongly indicating that the presence of the aziridine ring in natural as well as synthetic compounds is essential for such activities.2 Due to known activity as pharmacophore, aziridine moiety attracted considerable attention to medicinal and synthetic organic chemists.3 In conducted research the (±)-halogenated marinoaziridine derivatives 1a-1h were prepared by reaction of variously substituted N-tosyl imines and achiral 2-quinolinone sulfonium salt in the presence of a base, as a mixture of cis and trans isomers in good yield. The diastereoselectivity of the reaction is different and depends on the imine substituent. In most cases, the trans isomer predominates, while unusual cis diastereoselectivity was observed in derivative 1d. In the second part of this research, the conditions of enantioseparation of newly synthesized compounds on polysaccharide chiral stationary phases based on amylose and cellulose derivatives were investigated using high performance liquid chromatography. The obtained results showed that the Chiral ART Cellulose SC stationary phase with selector cellulose tris- (3, 5-dichlorophenylcarbamate) proved to be the best choice in the enantioseparation

enantiomeri ; dijastereoizomeri ; 2-kinolinoni ; marinoaziridini ; N-tosil imini ; sumporovi ilidi ; totalna sinteza

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