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Open Access Publications from the University of California

Intramolecular Diels-Alder Reactions in Organic Synthesis

  • Author(s): Sizemore, Nicholas Blandford Luke
  • Advisor(s): Rychnovsky, Scott D.
  • et al.

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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