β-Carbolines are a subclass of nitrogen-containing heterocyclyes that are ubiquitous in nature. Our efforts have focused on the rapid synthesis of these molecules using efficient methods. We will describe two strategies for the synthesis of β-carbolines using palladium-catalyzed reactions. First, we will describe our synthesis of eudistomin U and 1-aryl analogs using a Suzuki cross coupling strategy. This has allowed us to perform structure-activity studies of the natural product. Second, we will describe novel intramolecular [2+2+2] cyclization reactions involving palladium catalysis for the synthesis of 3,4-annulated β-carbolines. Our results with respect to the size of the annulation and the electronic requirements of the substrates indicate that the reaction is general. These projects demonstrate that palladium is an indispensable metal in heterocycle synthesis. Furthermore, its continued use can often uncover mechanistically unique reactivity.

Efficient palladium-catalyzed reactions toward complex nitrogen-containing heterocycles

249th National Meeting (2015)

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