Chemical Structure Data File for C.R. Whitlock's dissertation, "Synthetic approaches to the dragmacidin alkaloids"

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University of Alabama Libraries
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This Structure Data File (sdf) is associated with the dissertation by C.R. Whitlock ( It was generated by the University of Alabama Libraries. The .sdf file is licensed under a Creative Commons Attribution 4.0 International License (
This sdf file supports the research found in Whitlock's dissertation. Its abstract states: "The goal of this research was to develop a practical synthesis of a bisindolylpiperazine through the study of piperazine and indole chemistry. A simple oxidation of piperazine, followed by the addition of indole, did not succeed. The dimerization of nortryptophan derivatives failed to give a piperazinedione that might have lead to a bisindolylpiperazine. An acylated alpha-aminoacetaldehyde derivative was converted to an acylated dimethoxypiperazine, which could not be condensed with indole. The first bisindolylpiperazinedione was synthesized when 1,4-dibenzylpiperazine-2,5-dione was brominated and then reacted with indole. An analogous sequence, starting with sarcosine anhydride also succeeded. This product as reduced to afford the first bisindolylpiperazine. Using this methodology, the first synthesis of a member of the dragmacidin series of alkaloids was accomplished, and the reported structure of the natural product dragmacidin B was confirmed."