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Exploration of the Interrupted Fischer Indolization Reaction and its Application Toward the Synthesis of Indoline-Containing Alkaloids

  • Author(s): Schammel, Alexander Wayne
  • Advisor(s): Garg, Neil K
  • et al.
Abstract

Chapter one discusses previous synthetic efforts toward the communesin alkaloids and perophoramidine. The chapter highlights not only new methods developed toward the communesin scaffold, but also the total syntheses of racemic and enantioenriched communesin alkaloids and perophoramidine. Chapters two, three, and four highlight our explorations of the interrupted Fischer indolization reaction. Chapter two details the development of our method to access the fused indoline scaffold, particularly the furoindoline and pyrrolidinoindoline motifs. Furthermore, this chapter discusses the formal synthesis of physovenine, the total synthesis of debromoflustramine B,

and the synthesis of the communesin scaffold, as well as methods to access enantioenriched furoindolines. Chapter three discusses how the interrupted Fischer indolization reaction was used to prepare the alzheimer's therapeutic candidate (+)-phenserine (a.k.a. Posiphen), in enantioenriched form. Finally, chapter four highlights the use of the interrupted Fischer indolization in a complex setting, with studies toward the communesin alkaloids and

perophoramidine.

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