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Bibliographic Record Display

• Author/Creator:Day, Joshua James.
  
• Title:Progress toward the total synthesis of actinophyllic acid [electronic resource].
  
• ISBN:9781124089089
  
• Physical Description:1 online resource (240 p.)
  
• Links:Online thesis
  

• Yale Holdings

  Holdings Record Display

  • Location:Yale Internet Resource
    Information about Off Campus Access
    
    
  • Call Number: None
    
  • Status:No information available 
  • Notes: Online resource
    

   
• Local Notes:Access is available to the Yale community.
  
• Notes:Source: Dissertation Abstracts International, Volume: 71-07, Section: B, page: 4255.
  Adviser: John L. Wood.
  
• Access and use:Access restricted by licensing agreement.
• Summary:The search for natural products with biological activity related to cardiovascular disorders resulted in the isolation and structure elucidation of the indole alkaloid actinophyllic acid in 2005 Following isolation from the leaves of Alstonia actinophylla it was found to inhibit carboxypeptidase U (CPU) with an IC50 of 0.84 microM using a CPU/hippuricase coupled enzyme assay.
  Efforts toward the total synthesis of actinophyllic acid are described, which includes two strategies. The first relied upon a sequential Michael addition/alkylation sequence to install the polycyclic carbon framework found in the natural product. The second strategy relied upon a more convergent route to the polycyclic core of actinophyllic acid. Both routes accessed intermediates possessing all carbon atoms requisite for the natural product. Highlights from these routes include a net amine conjugate addition through the intermediacy of a phosphonium salt and formation of a quaternary carbon by trapping a putative aza-isobenzofulvene intermediate with an enamine nucleophile, respectively.
  
• In_:Dissertation Abstracts International 71-07B.
  
• Format:Book
• Thesis note:Thesis (Ph.D.)--Yale University, 2010.
  
• Also listed under:Yale University.