• deuteration
• isoprostanes
• natural compounds
• olefin metathesis
• stereoselective synthesis

Isoprostanes (IsoPs) are natural compounds generated in vivo through the autoxidation of polyunsaturated fatty acids. Due to their formation mechanism, IsoPs are among the best biomarkers to assess oxidative stress (OS), a condition known to be involved in the onset and progression of numerous human and animal diseases. Moreover, preliminary studies have demonstrated that these compounds exert significant biological activity, which encourages further investigation, including their potential pharmaceutical applications.
Both aforementioned objectives require the availability of suitable and possibly cost-effective synthetic standards, including labeled compounds.
In order to obtain reference samples for the identification of an unknown component found in the HPLC-MS analysis of biological fluids, the first part of this Master's Thesis explored several approaches aimed at synthesizing diastereoisomers of 15-F2t-IsoP. Although it was not possible to establish with certainty the structure of the unknown compound, the results obtained allow to narrow down the number of possible candidates.
In the second part of the work, a new approach was developed to prepare a stereodefined precursor in deuterated form, introducing deuterium atoms into the central "core" of the cyclopentane ring. Using a synthetic pathway developed in our laboratory, the intermediate thus obtained can be exploited to obtain isoprostanoid compounds in labeled form.