Peroxycarbenium ions as versatile synthetic intermediates for the construction of cyclic organic peroxides, and studies towards the asymmetric synthesis of (+)-artemisinin.

摘要

This dissertation discusses the design, development, and reactivity of silyl peroxyketals for the generation of peroxycarbenium ions, and application of these intermediates in [3 + 2] and [3 + 3] annulation reactions with alkenes. This methodology was used for the preparation of plakinic acid natural product analogues. Furthermore, through our studies on the construction of the peroxide moiety, we discovered a cascade reaction between ketoalkenes and H2O 2 that provided access to the medicinally important 1,2,4-trioxane pharmacophore. We attempted to expand the scope of the cascade reaction to more complicated systems, which involved studies directed towards the asymmetric synthesis of (+)-artemisinin.