This Structure Data File (sdf) is associated with the dissertation by T.V. Hughes (http://library.ua.edu/vwebv/holdingsInfo?bibId=1016924). It was generated by the University of Alabama Libraries. The .sdf file is licensed under a Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0/).
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This sdf file supports the research found in Hughes' dissertation. Its abstract states: "This dissertation consists of four chapters. The first chapter details the progress toward a total synthesis of securine A (1). Securine A is an indole/imidazole containing marine alkaloid which contains a 2,3-disubstituted indole ring and a 4,5-disubstituted imidazole ring with a 12-membered lactam connecting the two. The approach into the securine A ring system utilized the opening of a pyrano[3,4-b]indol-3-one ring system with a modified histamine derivative. Efforts in the synthesis of securine A were not successful, but the synthesis of a similar analogue, compound 53, which contained a 13-membered ring was achieved.
Chapter two deals with the total synthesis of the indole/maleimide/imidazole containing marine alkaloids: the didemnimides A–D (84– 87). The total syntheses of didemnimide A–D were successful and utilized a base catalyzed condensation reaction of methyl indolyl-3-glyoxylate (102) and 1-trityl-4-imidazoleacetamide (104).
Chapter three details a new and convenient synthesis of 1-cyanobenzotriazole (123) and efforts to use it as a source of +CN in carbon-carbon forming reactions. The synthesis is safer than previously reported methods and allows for 123 to be made in multi-gram scale rather inexpensively. It was demonstrated that 1-cyanobenzotriazole (123) is a good source of +CN in carbon-carbon forming reactions by reacting with a variety of sp3, Sp 2, and sp carbanions.
Chapter four details a new synthesis of hexadecylquinolinium tricyanoquinodimethanide (171) which has been shown to be a molecular rectifier. In search of additional molecular rectifiers, this new methodology was applied to the synthesis of Z-β-(N-n-hexadecyl-2-benzothiazolium)-α-cyano-4-styryldicyanomethanide (181) as well as its selenium and tellurium analogues 190 and 200; respectively. Additionally, the synthesis of other T-D+-π-A- types of molecules was explored in search for other molecular rectifiers. However, of all the compounds synthesized herein, only 171 has been shown to rectify."
