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Open Access Publications from the University of California

Synthetic Approaches to Indole Alkaloids and Biosynthetic Investigations of the Echinocandins and Chaetoviridins

  • Author(s): Chiou, Grace
  • Advisor(s): Garg, Neil K
  • et al.

Chapter one discusses the previous use of synthetic chemistry in biosynthetic studies of natural products. Emphasis is given to more recent work concerning the brevianamide, notoamide, and communesin fungal indole alkaloids. Chapters two and three highlight our explorations of the interrupted Fischer indolization reaction to access indoline containing natural products. Specifically, chapter two focuses on the use of the interrupted Fischer indolization reaction to prepare the Alzheimer's therapeutic candidate, (+)-phenserine (a.k.a. Posiphen), in enantioenriched form. Chapter three is a discussion of our studies to use the interrupted Fischer indolization reaction towards syntheses of the communesin alkaloids and perophoramidine.

Chapters four, five, and six present our use of chemical synthesis in the discussion of elucidating the biosynthetic pathways of natural products. In particular, chapter four focuses on the echinocandin lipopeptides and our efforts to identify and characterize the biochemical pathway utilized by nature. Chapters five and six highlight our work to determine the biosynthesis of the chaetoviridin polyketides. In addition, a strategy for introducing structural diversity into polyketides is reported.

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