Lewis Acid-Mediated Diastereoselective Synthesis of Medium-Sized Cyclic Ethers and Studies Towards the Synthesis of Plakortolide E and 6-Epiplakortolide E
Date of Award
Doctor of Philosophy (PhD)
Arun K. Ghosh
Committee Member 1
Committee Member 2
Committee Member 3
The Lewis acid-mediated synthesis of medium-sized cyclic ethers has been achieved in a diastereoselective manner. Using TMSOTf or BF3•OEt2, we developed a novel protocol for the intermolecular synthesis of eight-membered cyclic ethers (oxocenes) via Prins-type cyclization. This methodology displays a unique approach towards 2,4,8-trisubstiituted oxocene cores, with good yields and excellent diastereoselectivity. We have also expanded this protocol to show applicability towards the synthesis of seven-membered rings (oxepines and oxepanes). Progress studies towards the synthesis of plakortolide E and 6-epiplakortolide E are described. Featuring a bicyclic peroxylactone, these compounds are of interest due to their potential antimalarial activity. A key step in these syntheses features a diastereoselective [4+2] cycloaddition with singlet oxygen, under photosensitized conditions.
Tomaine, Anthony J., "Lewis Acid-Mediated Diastereoselective Synthesis of Medium-Sized Cyclic Ethers and Studies Towards the Synthesis of Plakortolide E and 6-Epiplakortolide E" (2018). Open Access Dissertations. 1835.