The Synthetic Methodology Towards the Construction of Spirocyclic Ethers

Student: Leslie Laguna (Chemistry Department )

Faculty Adviser: Ruquia Ahmed-Schofield (Chemistry Department)

Abstract

Many natural and biologically important molecules contain spirocyclic ethers as part of their structure.  This structural feature is naturally found in tea, vanilla, and red wine grape skins and has been a major component of various medications for cardiovascular disease, antitumor, sedation, and uterotonics.  Our approach towards the construction of spirocyclic ethers involves the photodecomposition of cyclic derivatives of Barton PTOC esters in the presence of alcohol nucleophiles. The variability within the synthetic process is substantial: the ring sizes may vary, the alcohol nucleophile may contain double or triple bonds and may also posses varying substituents, and the benzaldehyde employed in the aldol addition reaction can be substituented to stabilize the radical cation intermediate.  Results of our model studies will be presented and, upon completion of these studies, we expect to apply of this methodology to the construction of more complex and biologically important molecules.



Click here for the research poster presented at the Fifth Annual Landmark Conference Summer Research Symposium