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A Concise Semisynthesis of Hederagonic Acid

C–H Activation in Natural Product Synthesis

  • Book
  • © 2020

Overview

Authors:
  1. Christian Knittl-Frank

    1. Institute of Organic Chemistry, University of Vienna, Vienna, Austria

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  • The shortest semisynthesis of this oleanane

Part of the book series: BestMasters (BEST)

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Table of contents (3 chapters)

  1. Front Matter

    Pages I-XIX
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  2. Introduction

    • Christian Knittl-Frank
    Pages 1-11

  3. Results and Discussion

    • Christian Knittl-Frank
    Pages 13-40

  4. Experimental Section

    • Christian Knittl-Frank
    Pages 41-55

  5. Back Matter

    Pages 57-60
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Keywords

About this book

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.

Authors and Affiliations

  • Institute of Organic Chemistry, University of Vienna, Vienna, Austria

    Christian Knittl-Frank

About 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.

Bibliographic Information

  • Book Title: A Concise Semisynthesis of Hederagonic Acid

  • Book Subtitle: C–H Activation in Natural Product Synthesis

  • Authors: Christian Knittl-Frank

  • Series Title: BestMasters

  • DOI: https://doi.org/10.1007/978-3-658-30011-1

  • Publisher: Springer Spektrum Wiesbaden

  • eBook Packages: Chemistry and Materials Science, Chemistry and Material Science (R0)

  • Copyright Information: The Editor(s) (if applicable) and The Author(s), under exclusive license to Springer Fachmedien Wiesbaden GmbH, part of Springer Nature 2020

  • Softcover ISBN: 978-3-658-30010-4Published: 07 April 2020

  • eBook ISBN: 978-3-658-30011-1Published: 06 April 2020

  • Series ISSN: 2625-3577

  • Series E-ISSN: 2625-3615

  • Edition Number: 1

  • Number of Pages: XIX, 60

  • Number of Illustrations: 1 b/w illustrations

  • Topics: Organic Chemistry, Catalysis, Chemistry/Food Science, general, Bioorganic Chemistry

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