Synthesis, X-ray Analysis, and Antiviral Evaluation of Allohimachalol: Insights into Stereoselectivity in Epoxidation

Allohimachalol, a vital element in Atlas cedar wood essential oil, is obtained through steam distillation, shaping the oil's distinctive aroma. Its prominence enhances the unique olfactory character of cedar oil, making it valuable in perfumery and aromatherapy. To enhance its reactivity, we conducted experimental and theoretical studies on the epoxidation reaction of Allohimachalol with meta-chloroperbenzoic acid (m-CPBA). This reaction led to the formation of a new product, referred to as product 3, through a simultaneous rearrangement process. The compound structures were identified using spectroscopic techniques, including 1H and 13C NMR, along with X-ray diffraction. Furthermore, the electronic structures of the synthesized compounds were investigated through theoretical calculations using density functional theory (DFT) at the B3LYP/6-311G(d,p) level. The analysis of energy profiles related to different reaction pathways produced results in line with the experimental observations, confirming the alignment of the allohimachalol epoxidation reaction with theoretical predictions. Additionally, a docking analysis was performed on the investigated compounds within the primary protease of SARS-CoV-2 (6LU7) and HIV, indicating that compound 3 holds promise as a potential antiviral drug for human health.