Application of Green Chiral Chromatography in Enantioseparation of Newly Synthesized Racemic Marinoepoxides

Buljan, Anđela; Roje, Marin (2022) Application of Green Chiral Chromatography in Enantioseparation of Newly Synthesized Racemic Marinoepoxides. Marine Drugs, 20 (8). ISSN 1660-3397

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Official URL: https://www.mdpi.com/1660-3397/20/8/530

Abstract

Enantioseparation of the newly synthesized series of novel quinoline- 2(1H)-one epoxide structures rac-6a–c and rac-8a–c, named marinoepoxides, is described. Marinoepoxide rac-6a, the key intermediate in the total synthesis of natural products marinoaziridines A and B, as well as their structural analogues, was synthesized by addition of the achiral ylide generated in situ from the sulfonium salt 5 or 7, to the carbon-oxygen double bond of the corresponding quinoline-2(1H)-one-4-carbaldehyde 4a–c in good yield. Separation of enantiomers of (±)-2, 3, 3-trisubstituted marinoepoxides rac-6a–c and (±)-trans-2, 3-disubstituted marinoepoxides rac-8a–c was studied using two immobilized polysaccharide type chiral stationary phases (CSPs) ; tris-(3, 5- dichlorophenylcarbamoyl)cellulose stationary phase (CHIRAL ART Cellulose-SC) and tris-(3, 5-dimethylphenylcarbamoyl)amylose stationary phase (CHIRAL ART Amylose-SA). Enantioseparation conditions were explored by high-performance liquid chromatography (HPLC) using dimethyl carbonate/alcohol mixtures and n-hexane/ethanol (80/20, v/v) as mobile phase, and by supercritical fluid chromatography (SFC) using CO2/alcohol mixtures as mobile phase. In all examined racemates, enantioseparation was successfully achieved, but its efficiency largely depended on the structure of chiral selector and type/composition of the mobile phase.

Item Type:

Article

Uncontrolled Keywords:

green solvents ; chiral chromatography ; marinoepoxides ; marinoaziridines ; 2, 3-disubstituted epoxides ; 2, 3, 3-trisubstituted epoxides ; enantioseparation ; supercritical fluid chromatography (SFC) ; high-performance liquid chromatography (HPLC) ; supercritical carbon dioxide ; dimethyl carbonate (DMC)

Subjects:

NATURAL SCIENCES > Chemistry

Divisions:

Division of Organic Chemistry and Biochemistry

Projects:

Project title	Project leader	Project code	Project type
Bioprospecting Jadranskog mora	Čož-Rakovac, Rozelinda; Dragović-Uzelac, Verica; Šantek, Božidar; Jokić, Stela; Jerković, Igor; Kraljević Pavelić, Sandra	KK.01.1.1.01.0002	EK

Depositing User:

Marin Roje

Date Deposited:

05 Sep 2022 12:18

URI:

http://fulir.irb.hr/id/eprint/7548

DOI:

10.3390/md20080530