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A Concise Semisynthesis of Hederagonic Acid

C–H Activation in Natural Product Synthesis

Christian Knittl-Frank (Autor)

Buch | Softcover

XIX, 60 Seiten

2020 | 1st ed. 2020
Springer Fachmedien Wiesbaden GmbH (Verlag)
978-3-658-30010-4 (ISBN)

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Christian 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.

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.

Hederagonic Acid and C-H Activation; Optimization of the Synthetic Sequence.- Final Synthetic Route to Hederagonic Acid.- Experimental Section.

Erscheinungsdatum	08.04.2020
Reihe/Serie	BestMasters
Zusatzinfo	XIX, 60 p. 1 illus.
Verlagsort	Wiesbaden
Sprache	englisch
Maße	148 x 210 mm
Gewicht	120 g
Themenwelt	Naturwissenschaften ► Biologie ► Biochemie
	Naturwissenschaften ► Chemie ► Organische Chemie
	Naturwissenschaften ► Chemie ► Physikalische Chemie
Schlagworte	C–H activation • C-H Activation • C-H Oxidation • C–H Oxidation • Hederagonic Acid • Multi-step One-pot Reaction • Natural Product Synthesis • Oleananes • triterpenoids
ISBN-10	3-658-30010-8 / 3658300108
ISBN-13	978-3-658-30010-4 / 9783658300104
Zustand	Neuware