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Development of multicomponent assembly processes and their application to the synthesis of novel heterocyclic scaffolds and the total synthesis of actinophyllic acid : application of an iminium ion mediated cascade

Several novel multicomponent assembly processes have been developed for the preparation of a diverse array of complex heterocyclic systems from relatively simple starting materials. These studies resulted in the discovery of a new quinazolone forming reaction, which was applied to the one-step synthesis of the quinazolinocarboline alkaloid rutaecarpine. Biological screening of these complex heterocycles culminated in the identification of a potent sigma-2 receptor ligand. A novel N-acyliminium ion mediated cascade reaction was employed for the concise synthesis of (±)-actinophyllic acid. The completion of the synthesis relied on the development of a reaction sequence that avoided a potentially detrimental fragmentation process. Furthermore, several anti-cancer compounds were identified through a diverted total synthesis approach. / text

Identiferoai:union.ndltd.org:UTEXAS/oai:repositories.lib.utexas.edu:2152/26089
Date22 September 2014
CreatorsGranger, Brett Adam
Source SetsUniversity of Texas
Detected LanguageEnglish
TypeThesis
Formatapplication/pdf

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