Model studies toward the total synthesis of lycolucine and the development of various synthetic methods

by 1976- Dinsmore, Jason Matthew

DINSMORE, JASON MATTHEW. Model Studies Toward the Total Synthesis of Lycolucine and the Development of Various Synthetic Methods. (Under the direction of Professor Daniel L. Comins.) A study directed at the total synthesis of lycolucine was carried out and is discussed within. Various synthetic routes were attempted toward this end. The synthetic schemes all revolve around utilization of the well-established N- acylpyridinium salt chemistry as the foundational method of synthesis. One approach employs metathesis chemistry to attempt the construction of a key carbon-carbon bond. A one-pot terminal alkene homologation was discovered. This investigation reveals the ability to homologate terminal alkenes by one carbon utilizing the 2nd generation Grubbs catalyst. Various aromatic and non-aromatic substrates were used to demonstrate the scope of the reaction, with yields ranging from 65% to 86%. This work reveals the first example of a one-pot one-carbon alkene homologation from an existing terminal alkene. A few synthetic methods, such as the formation of indolizidine scaffolds and amino alcohols, are also discussed. Various compounds were realized that could potentially lead to the development of more complex structures.