Please use this identifier to cite or link to this item: http://earsiv.odu.edu.tr:8080/xmlui/handle/11489/2674
Title: A novel and stereoselective synthesis of 2-bromo-6-chloro-5-methylcyclohex-4-ene-1,3-diyl diacetate: conduritol-A derivative
Authors: Kaplan, Dilek
Kelebekli, Latif
Ordu Üniversitesi
Keywords: Dihalogen cyclitol; Dihaloconduritol; Cyclitol; Dihaloconduritol-A derivative
STEREOSPECIFIC SYNTHESIS; EPOXIDES; BROMOCONDURITOL; METABOLITES
Issue Date: 2020
Publisher: SPRINGER, ONE NEW YORK PLAZA, SUITE 4600, NEW YORK, NY, UNITED STATES
Abstract: The stereoselective synthesis of 2-bromo-6-chloro-5-methylcyclohex-4-ene-1,3-diyl diacetate, methyl-substituted dihaloconduritol-A is reported. Bromination of 2-methylbenzo-1,4-quinone followed by the reduction in the carbonyl groups with NaBH4 to give a dioldibromo compound. The diol was converted to diacetates by acetylation with Ac2O-pyridine. Reaction of methyl-dioldibromodiacetate with LiOH gave stereoselectively the monoepoxide compound. Controlled reaction of the epoxide with AcCl in methylene chloride furnished the desired new dihaloconduritol-A derivative which was characterized by spectroscopic methods. All the synthesized compounds were characterized by FT-IR, H-1-NMR, C-13-NMR, COSY (2D-NMR), and HRMS analyses.
URI: http://doi.org/10.1007/s13738-019-01810-3
http://earsiv.odu.edu.tr:8080/xmlui/handle/11489/2674
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