Intramolecular Diels-Alder Reactions in Organic Synthesis

Doctoral thesis English OPEN
Sizemore, Nicholas Blandford Luke (2014)
  • Publisher: eScholarship, University of California
  • Subject: Chemistry | Organic chemistry | computational chemistry | Intramolecular Diels-Alder reaction | maoecrystal Z | palhinine | synthetic organic chemistry

Intramolecular Diels-Alder (IMDA) reactions are an important class of reactions in synthetic organic chemistry for the rapid construction of polycyclic frameworks. Three classes of IMDA reactions were investigated synthetically and computationally: 1) all-carbon type 1 IMDA reactions, 2) N-acylnitroso type 2 IMDA reactions, and 3) cyano-azadiene IMDA reactions. The first class was implemented in research toward the total synthesis of maoecrystal Z and isopalhinine A. The second class was studied computationally to understand the origins of regio- and stereochemistry in these reactions. The third class was investigated in the context of indolizine and quinolizidine synthesis.
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