"Cascade reactions west of the Cascades".
Abstract: I will discuss the development of cascade reactions for the synthesis of natural products in two parts: developing radical reactions for alkaloid synthesis, and using pericyclic reaction cascades for the synthesis of molecules with conformational chirality. In the first part, our work toward alkaloid synthesis seeks to capitalize on the reactivity of carbon-centered radicals in nitrogen-rich functional groups. Radicals are generally tolerant of acidic hydrogen atoms, heteroatom lone pairs, and other functional groups with delicate acid/base reactivity. As a result, radical reactions can be particularly effective in alkaloid synthesis.
In the second part of the talk, I will discuss our work synthesizing and studying the conformational behavior of complex cyclophane, biaryl, and diphenyl ether natural products. Such molecules often have misunderstood chiral properties. I will present our efforts to synthesize these molecules and determine their racemization rate.
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