Date of Award
College of Natural and Health Sciences
Dr. Ralph Salvatore
Cyclopropyl acetylene (CA) is a key intermediate in the synthesis of the human immunodeficiency virus (HIV) reverse transcriptase inhibitor, Efavirenz (EFV), an antiviral drug used to treat HIV. CA is an expensive raw material, difficult to obtain, and employed in the preparation of medications to combat acquired immunodeficiency syndrome (AIDS). It was found that the structure could be synthesized by the utilization of PCl5; however, this resulted in unwanted ring opening products. To address this issue, a one pot synthesis was developed using Ph3PCl2 as a mild chlorinating agent. In addition, a new analog has been proposed substituting the cyclopropyl group for alternative cyclic hydrocarbons. Instead of using a cyclopropyl ring, a larger ring with more than three carbons can result in less ring strain and subsequently, less ring opening. Previous experiments have tested other ring structures; however, larger cyclic hydrocarbons have yet to be studied within these conditions. Efforts toward the synthesis of higher order analogs including cyclobutyl acetylene will be discussed once the optimal yield using a variety of bases for the synthesis is determined. Various reaction procedures are detailed
Bautista, Elizabeth S., "VARIOUS SYNTHETIC PATHWAYS TOWARDS EFAVIRENZ AND ITS ANALOGS; THE REPLACEMENT OF THE SIDE CHAIN" (2023). Selected Honors Theses. 176.