Synthetic studies towards vibsanin E and photochemical assisted [4+2] cycloadditions
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The primary objective of this work was to explore a total synthesis of the natural product vibsanin E. A key reaction toward this natural product is the [4+3] cycloaddition methodology developed in the Davies group which sets up the core ring system of the target molecule. The two side chains of the natural product were envisioned to be introduced by a UV assisted [4+2] cycloaddition strategy, but unfortunately this eventually gave a product epimeric with vibsanin E, 5- epi -10- epi -vibsanin E. The diastereomeric outcome of this UV assisted [4+2] cycloaddition initiated a second project where investigations into the regiochemical and diastereomeric outcome of the reaction was explored. The methodology was successfully explored with a variety of dienes and several enones.