20.500.12556/RUL-129732 Uporaba pericikličnih reakcij v ključnih stopnjah sinteze naravnih spojin Application of pericyclic reactions as key steps during the synthesis of natural compounds 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. 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. cikloadicija 2H-piran-2-oni periciklične reakcije sinteza naravnih snovi Diels–Alderjeva reakcija cycloaddition 2H-pyran-2-ones pericyclic reactions synthesis of natural compounds Diels–Alder reaction true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2021-09-07 13:15:00 2021-09-07 13:15:01 2022-09-09 04:13:01 0000-00-00 00:00:00 2021 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 14021 79514115 Subic_Ziga_-_Uporaba_periciklicnih_reakcij_v_kljucnih_stopnjah_sinteze_naravnih_spojin.pdf Subic_Ziga_-_Uporaba_periciklicnih_reakcij_v_kljucnih_stopnjah_sinteze_naravnih_spojin.pdf 1 0F9A9CE9D5FE61E8190B3D1C774CD70D 6914bc3f3c72755c123fcd2084128abebf8d8c1dabb28bfeaa109bc1251a8195 9988063e-0fcc-11ec-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=146758 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0