Total Synthesis of Plakortide E and Biomimetic Synthesis of Plakortone B

  • Xiao-Yu Sun

Part of the Springer Theses book series (Springer Theses)

Table of contents

  1. Front Matter
    Pages i-xiv
  2. Xiao-Yu Sun
    Pages 1-19
  3. Xiao-Yu Sun
    Pages 21-76
  4. Xiao-Yu Sun
    Pages 77-78
  5. Xiao-Yu Sun
    Pages 79-126
  6. Back Matter
    Pages 127-220

About this book

Introduction

In his thesis, Xiao-yu Sun conducts the first total synthesis of all possible stereoisomers of plakortide E and also confirms the absolute configuration of natural plakortide E. Xiao-yu Sun subsequently converts Plakortide E methyl ester to plakortone B in a biomimetic conversion. Construction and functionalization of cyclic peroxides are notoriously difficult due to the very low O-O bond dissociation energy. Plaktoride E is isolated from the Jamaican marine sponge platorits halichondrioides and contains a five-membered peroxide ring, with oxygen atoms linked to tertiary C4 and C6 centers. The methodology used for synthesizing highly substituted cyclic peroxides is novel and useful, and not only extends the field of Pd-catalyzed reactions, but also provides a convenient synthetic approach for the preparation of the 1,2-dioxolanes series. Plakortide E and plakortone B are bioactive, which means that the synthetic studies on them and their analogs are pivotal in drug discovery.

Keywords

Springer Thesis Prize biomimetic synthesis of plakortone B cascade reaction lipase-catalyzed kinetic resolution metal-halogen exchange on cyclic peroxides total synthesis of plakortide E

Authors and affiliations

  • Xiao-Yu Sun
    • 1
  1. 1.Lab. of Organic ChemistryETH ZürichZürichSwitzerland

Bibliographic information

  • DOI https://doi.org/10.1007/978-3-642-27195-3
  • Copyright Information Springer-Verlag Berlin Heidelberg 2012
  • Publisher Name Springer, Berlin, Heidelberg
  • eBook Packages Chemistry and Materials Science
  • Print ISBN 978-3-642-27194-6
  • Online ISBN 978-3-642-27195-3
  • About this book
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