The Arndt–Eistert homologation

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Table of contents

Résumé du travail
Chapter 1 Dual organocatalysis in enantioselective synthesis of bicyclo[3.2.1]octanes .
1.1. Introduction
1.1.1. Organocatalysis: concepts, main activation modes & multi-catalysis
1.1.2. Objective of the research project
1.1.3. Single step enantioselective construction of bicyclo[3.2.1]octanes .
1.2. Original enantioselective bi-organocatalytic synthesis of bicyclo[3.2.1]octanes
1.2.1. Preparation of substrates
1.2.2. Early work
1.2.3. Enantioselective synthesis of bicyclo[3.2.1]octanes
1.2.4. Conclusion
Chapter 2 Total synthesis of quadrane sesquiterpenes
2.1. Introduction
2.1.1. Quadranes natural products
2.1.2. Total syntheses of quadranes
2.1.3. Retrosynthetic analysis for (–)-isishippuric acid B (VI)
2.2. Synthetic approach to (–)-isishippuric acid B (VI)
2.2.1. Construction of the bicyclo[3.2.1]octane
2.2.2. Functionalization at C2
2.3. Total synthesis of (+)-suberosanone (IV) and formal synthesis of (+)-suberosenone (III)
2.3.1. Retrosynthetic analysis
2.3.2. The Arndt–Eistert homologation
2.3.3. Completion of the syntheses
2.4. Summary and conclusion
Chapter 3 Enantioselective synthesis of glutarimides
3.1. Introduction
3.1.1. Glutarimides in drugs and natural products
3.1.2. Enantioselective routes to glutarimides
3.1.3. Our approach
3.2. Enantioselective synthesis of glutarimides
3.2.1. The racemic series
3.2.2. The optically active series
3.3. Conclusion
General conclusion
Experimental part
ES.0. General experimental information
ES.1. Chemistry of bicyclo[3.n.1]octanes
ES.2. Total synthesis of quadrane sesquiterpenes
ES.3. Chemistry of glurarimides