Exploring new methodologies for the synthesis of garlic metabolites

The therapeutic benefits of garlic are related to the high concentrations of organosulfur compounds present. Allicin is the main biologically active component of garlic extracts. Due to its instability, it rapidly decomposes into a variety of organosulfur compounds. Among the decomposition products of allicin, ajoene is biologically more stable and active. In this thesis, an efficient total synthesis of ajoene was accomplished from easily available starting materials. In addition, the protocol allowed the synthesis of several ajoene derivatives. Moreover, the protocol proved to be amendable to scale-up and provided 169g of ajoene in ~90% purity. A second synthetic protocol for the synthesis of ajoene from simple and easily available starting materials has also been investigated in batch and in flow. Finally, a rapid, versatile and selective oxidation system has been developed for a variety of sulfides and disulfides. The method allowed the synthesis of allicin in moderate yields