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Date of Award
Restricted Thesis: Campus only access
Bachelor of Science
Dr. John Gupton
Dr. Wade Downey
Vinamidinium salts and β-chloroenals were utilized for the development of two synthetic routes towards the biologically active marine alkaloid Lamellarin G trimethyl ether. Both routes culminated at a key intermediate previously prepared by Wolfgang Steglich and co-workers in their total synthesis of Lamellarin G trimethyl ether. The route employing vinamidinium salts reached the Steglich synthon in ten steps and is modular in nature, making it amenable for structure activity relationship studies. The path involving β-chloroenals yielded the Steglich synthon in nine steps and is well suited for the rapid construction of the highly substituted pyrrole core of the natural product.
Giglio, Benjamin, "Relay total synthesis of lamellarin G trimethyl ether" (2009). Honors Theses. 631.