Application of carbon-hydrogen activation/Cope rearrangement methodology towards the total syntheses of Pseudopterosin, Elisabethatriene and Vinigrol
Brekan, Jonathan Alan
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C-H functionalization by means of rhodium carbenoid induced C-H insertion provides new strategies for the construction of C-C bonds. The success of this methodology is attributed to the combination of the donor/acceptor-substituted carbenoids and the dirhodium tetraprolinate catalysts. Recent results have shown that C-H insertion into allylic C-H bonds through utilization of vinyldiazoacetates provide Cope rearrangement products with high diastereoselectivities and enantioselectivities. This thesis is centered around the application of this 'combined' C-H activation/Cope rearrangement methodology towards the total synthesis of diterpene natural products: specifically, Pseudopterosin, Elisabethatriene and Vinigrol.