New Gold-Catalyzed Reactions and Applications for the Synthesis of Alkaloids

1. Front Matter

   Pages i-xiii

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2. Introduction

   • Ana Escribano Cuesta

   Pages 1-35

3. Gold(I)-Catalyzed Reactions of 1,6-Enynes with Aldehydes: Cycloaddition Versus Metathesis-Type Reactions

   • Ana Escribano Cuesta

   Pages 37-59

4. Formation of Cyclobutene Compounds via Gold(I)-Catalyzed Cycloisomerization of 1,n-Enynes

   • Ana Escribano Cuesta

   Pages 61-103

5. Approach Toward the Total Synthesis of Lundurines

   • Escribano Cuesta Ana

   Pages 105-189

6. Summary and Outlook

   • Ana Escribano Cuesta

   Pages 191-195

Ana Escribano Cuesta's thesis presents a detailed study of the inter- and intramolecular reactions of carbonyl compounds with 1,6-enynes using gold (I) complexes. An important part of the work involved streamlining the variables that allow the selective synthesis of different products such as tricyclic compounds, dihydropyrans, 1,3-dienes or cyclobutenes. The second chapter highlights the importance and difficulties in synthesising a cyclobutene subunit and the author includes a detailed description of how the products were prepared. The final chapter outlines the synthesis of lundurines using methodology developed by the author's research group for intramolecular gold-catalyzed cyclization of indoles with alkynes. The lundurine products developed in this work show significant in vitro cytoxicity toward B16 melanoma cells. The work in this thesis has led to a number of publications in high-profile chemistry journals.

• Antonio M. Echavarren
• Cyclization of Alkynylindole
• Cyclobutene Compounds
• Gold Properties
• Gold(I)-Catalyzed Cycloisomerization
• Gold-Catalyzed Nucleophilic Additions
• Indoloazocine Framework
• Lundurines A-D
• Metal-Catalyzed Alkyne Activation
• Total Synthesis of Lundurines

• Lead Optimization Fungicides, BASF SE., Ludwigshafen, Germany

  Ana Escribano Cuesta

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