Selektivne redukcije pripojenih piran-2-onov

Hrastar, Matic (author), Požgan, Franc (mentor)

Kumarini (2H-1-benzopiran-2-oni), ki jih najdemo v mnogo rastlinah, glivah in nekaterih mikroorganizmih, so vključeni v različnih procesih, kot so obrambni mehanizmi pred bakterijami, stresnimi dejavniki okolja in pri regulaciji hormonov. Zaradi različnih farmakoloških lastnosti kumarini pritegnejo veliko zanimanja za sintezo njihovih derivatov, kot novih terapevtskih sredstev. Tema moje diplome se osredotoča na redukcijo pripojenih 5-oksopiran-2-onov. Z uporabo primernih reakcij smo uspeli selektivno reducirati pripojene 5-oksopiran-2-one do željenih alkoholov, kjer smo kot reducent uporabljali NaBH4. Poskusili smo tudi reducirati ketonsko skupino s hidrogeniranjem s prenosom vodika ob prisotnosti rutenijevega katalizatorja in bioorgansko transformacijo ketona z uporabo gliv kvasovk.

• Language: Slovenian
• Keywords: kumarin
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: PEF - Faculty of Education
• Year: 2016
• PID: 20.500.12556/RUL-87133
• COBISS.SI-ID: 11338569
• Publication date in RUL: 04.09.2017

HRASTAR, Matic, 2016, Selektivne redukcije pripojenih piran-2-onov [online]. Bachelor’s thesis. [Accessed 25 March 2025]. Retrieved from: http://pefprints.pef.uni-lj.si/4165/

Secondary language

• Language: English
• Title: Selective reduction of fused pyran-2-ones

Abstract

Coumarins (2H-1-benzopyran-2-ones) found in plants, fungi and some microorganisms are involved in various processes, such as defense mechanisms against bacteria, abiotic stress and hormone regulation. Due to their various pharmacological properties they attract a lot of interest for the synthesis of their derivates. The theme of my diploma focuses on the reduction of fused 5-oxopyran-2-ones. We used a variety of conditions for reducing fused 5-oxopyran-2-ones to desired alcohols where NaBH4 was used as reducing agent. We tried to reduce ketone group with asymmetric transfer hydrogenation in the presence of Ru-catalyst and a bioorganic transformation of ketone with baker’s yeast.

• Keywords: coumarin