Selectivity in the Synthesis of Cyclic Sulfonamides

Application in the Synthesis of Natural Products

  • Kimberly Geoghegan
Part of the Springer Theses book series (Springer Theses)

Table of contents

  1. Front Matter
    Pages i-xiii
  2. Kimberly Geoghegan
    Pages 1-15
  3. Kimberly Geoghegan
    Pages 67-79
  4. Kimberly Geoghegan
    Pages 81-141
  5. Back Matter
    Pages 143-151

About this book

Introduction

In the area of organic chemistry one major challenge we are currently faced with is how to assemble potentially useful molecules in new ways that generate molecular complexity and in sequences that are as efficient as possible. Our efforts in this regard, specifically for the preparation of amino containing compounds incorporating an aromatic ring, are described in this doctoral thesis. We discovered an interesting regioselectivity in an intramolecular Heck reaction, which we studied for a series of substrates that are unbiased in terms of the size of the newly formed ring, where very high levels of selectivity in relation to the new carbon-carbon bond are typically observed. DFT calculations were performed to attempt to shed light on the reaction sequence. This regioselective Heck reaction, combined with the reductive removal of the temporary amino-protecting group, allowed us to synthesize the Sceletium alkaloids: mesembrane, mesembranol and mesembrine.

Keywords

Cyclic Sulfonamides Generation of All-Carbon Quaternary Centres Intramolecular Heck Reaction Multi-Task Catalysis Natural Product Synthesis One-Pot Heck Olefination-Hydrogenation Reaction Overman Rearrangment Regioselectivity in the Intramolecular Heck Reaction Synthesis of Sceletium Alkaloids Mesembrane and Mesembrine Wagner-Meerwein-Type Rearrangement

Authors and affiliations

  • Kimberly Geoghegan
    • 1
  1. 1.HCI F 308ETH ZürichZürichSwitzerland

Bibliographic information

  • DOI https://doi.org/10.1007/978-3-319-10338-9
  • Copyright Information Springer International Publishing Switzerland 2014
  • Publisher Name Springer, Cham
  • eBook Packages Chemistry and Materials Science
  • Print ISBN 978-3-319-10337-2
  • Online ISBN 978-3-319-10338-9
  • Series Print ISSN 2190-5053
  • Series Online ISSN 2190-5061
  • About this book