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Uporaba pericikličnih reakcij v ključnih stopnjah sinteze naravnih spojin
ID Šubic, Žiga (Author), ID Kranjc, Krištof (Mentor) More about this mentor... This link opens in a new window

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Abstract
V začetnih odstavkih v diplomskem delu najprej predstavim različne vrste pericikličnih reakcij, ki so podprte s shemami. S to razčlenitvijo se nato osredotočim na glavno tematiko mojega diplomskega dela, ki je povezana z reakcijami cikloadicije. Podrobno se pri cikloadicijah osredotočim na Diels–Alderjevo reakcijo, kjer poleg osnovne razlage predstavim tudi vrste spojin, ki so udeležene v reakciji, in nekatere njihove lastnosti, ki so večinoma povezane z reaktivnostjo. Na kratko opišem tudi regio- in stereoselektivnost reakcij in dodam odstavek o Woodward–Hoffmannovih pravilih, ki pojasnjujejo teoretično ozadje. Pregledu literature sledi drugo veliko poglavje – sinteze naravnih spojin, v katerem najprej predstavim spojino taksol s pomočjo starejšega in novejšega načina sinteze. Sledijo štirje primeri moderne sinteze naravnih spojin, kjer se v ključnih vlogah pojavi reakcija cikloadicije oziroma bolj natančno Diels-Alderjeva reakcija. Pomembni deli sintez so podprti z ustreznimi shemami. Naslednji odstavek sem namenil kratki predstavitvi piranonov, kjer na kratko predstavim oba regioizomerna predstavnika in navedem nekaj razlik med njima. V nadaljevanju opišem štiri primere sinteze naravnih spojin kjer nastopajo piranoni ali njihovi derivati. Tudi te sinteze so modernega tipa in predstavijo pomembnost piranonskega skeleta pri sintezi naravnih spojin. Zadnji odstavek namenim nekaj pomembnim 2H-piran-2-onskim spojinam, ki jih najdemo v naravi.

Language:Slovenian
Keywords:cikloadicija, 2H-piran-2-oni, periciklične reakcije, sinteza naravnih snovi, Diels–Alderjeva reakcija
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2021
PID:20.500.12556/RUL-129732 This link opens in a new window
COBISS.SI-ID:79514115 This link opens in a new window
Publication date in RUL:07.09.2021
Views:1607
Downloads:100
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Secondary language

Language:English
Title:Application of pericyclic reactions as key steps during the synthesis of natural compounds
Abstract:
In the first few paragraphs of my diploma work I present different types of pericyclic reactions, that are supported with schemes. Thereafter, I focus on the main theme of my work, which is connected to cycloaddition reactions. Specifically, I focus on the Diels–Alder reaction, where I describe the types of compounds that can engage in the reaction and elaborate on a few of their characteristics, that are mainly connected to their reactivity. I also dedicate a few paragraphs to regio- and stereoselectivity of these reactions and also include a short paragraph describing Woodward–Hoffmann rules that describe their theoretical background. After literary overview comes the second important chapter, namely, synthesis of natural compounds, where I firstly present the compound taxol with an older and a more contemporary example of its synthesis. Following that are four modern examples of natural compound synthesis, where the Diels–Alder reaction appears in key steps of the synthetic sequence. Important parts of the synthetic protocols are supported by schemes. The next paragraph is dedicated to pyranones, where I briefly present both regioisomers and point out a few differences between them. In continuation I describe 4 different examples of natural compound synthesis, in which pyranone or their derivatives are present as essential ingredients. In the last paragraph I briefly describe a few of the important 2H-pyran-2-ones, that can be found in nature.

Keywords:cycloaddition, 2H-pyran-2-ones, pericyclic reactions, synthesis of natural compounds, Diels–Alder reaction

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