LEADER 03790nam 22006135 450 001 9910410048603321 005 20200704074450.0 010 $a3-658-30011-6 024 7 $a10.1007/978-3-658-30011-1 035 $a(CKB)4100000010952060 035 $a(DE-He213)978-3-658-30011-1 035 $a(MiAaPQ)EBC6162733 035 $a(PPN)243760280 035 $a(EXLCZ)994100000010952060 100 $a20200406d2020 u| 0 101 0 $aeng 135 $aurnn|008mamaa 181 $ctxt$2rdacontent 182 $cc$2rdamedia 183 $acr$2rdacarrier 200 12$aA Concise Semisynthesis of Hederagonic Acid $eC?H Activation in Natural Product Synthesis /$fby Christian Knittl-Frank 205 $a1st ed. 2020. 210 1$aWiesbaden :$cSpringer Fachmedien Wiesbaden :$cImprint: Springer Spektrum,$d2020. 215 $a1 online resource (XIX, 60 p. 1 illus.) 225 1 $aBestMasters,$x2625-3577 311 $a3-658-30010-8 327 $aHederagonic Acid and C?H Activation; Optimization of the Synthetic Sequence -- Final Synthetic Route to Hederagonic Acid -- Experimental Section. 330 $aChristian Knittl-Frank reports on the development of a novel synthetic route to the naturally occurring polyhydroxylated oleanane, hederagonic acid. Polyhydroxylated oleananes are a vast family of naturally occurring triterpenoids with versatile biological activities. A low commercial availability combined with high prices make these molecules interesting targets in natural product synthesis. The developed synthetic approach starts from oleanolic acid, a cheap material that is commercially available in bulk quantities. It features several multi-step one-pot reactions, allowing a minimization of the number of steps and reducing the preparative effort. Importantly, catalytic C?H functionalization was achieved at unusually low temperatures. Hederagonic acid was thus prepared in as little as four steps, resulting in the shortest semisynthesis of this oleanane to date. Contents Hederagonic Acid and C?H Activation; Optimization of the Synthetic Sequence Final Synthetic Route to Hederagonic Acid Experimental Section Target Groups Scientists and students in the field of organic chemistry, especially natural product synthesis The Author Christian Knittl-Frank is currently pursuing his PhD studies, focusing on natural product synthesis and synthetic methodology, at the Department of Organic Chemistry, University of Vienna, Austria. He is part of the MolTag doctoral program that aims to development new molecular drugs targeting ion channels. . 410 0$aBestMasters,$x2625-3577 606 $aOrganic chemistry 606 $aCatalysis 606 $aChemistry 606 $aBioorganic chemistry 606 $aOrganic Chemistry$3https://scigraph.springernature.com/ontologies/product-market-codes/C19007 606 $aCatalysis$3https://scigraph.springernature.com/ontologies/product-market-codes/C29000 606 $aChemistry/Food Science, general$3https://scigraph.springernature.com/ontologies/product-market-codes/C00004 606 $aBioorganic Chemistry$3https://scigraph.springernature.com/ontologies/product-market-codes/C19010 615 0$aOrganic chemistry. 615 0$aCatalysis. 615 0$aChemistry. 615 0$aBioorganic chemistry. 615 14$aOrganic Chemistry. 615 24$aCatalysis. 615 24$aChemistry/Food Science, general. 615 24$aBioorganic Chemistry. 676 $a547.2 700 $aKnittl-Frank$b Christian$4aut$4http://id.loc.gov/vocabulary/relators/aut$01065321 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910410048603321 996 $aA Concise Semisynthesis of Hederagonic Acid$92544653 997 $aUNINA