The study of indoles, one of the most prevalent classes of alkaloids, is a rich area of research that has spanned over one hundred and fifty years. Access of this core structure includes classic reactions such as the Fischer indole synthesis, Larock indole synthesis, and many more. More recently, the Söderberg research lab has accessed indoles via the CO-mediated N-heterocyclization of <i>ortho</i>-nitrostyrene derivatives. This reductive cyclization has proven useful in a number of synthetic endeavors as a means of late-stage access of the indole core. Recently, our attention has turned to dilemmaones A-C, three indole alkaloids isolated from a collection of marine sponges found off the coast of South Africa in 1998. These compounds, in addition to their promising data from initial cytotoxicity screening, are interesting synthetic targets due to the unusual presence of either a hydroxymethylene or methoxymethylene at the C2 position. Key strategies in our synthetic efforts toward the dilemmaones include a palladium-catalyzed cross-coupling to introduce the C2 and C3 positions of the target molecule and late-stage application of the N-heterocyclization to form the indole core.

Synthetic studies toward dilemmaones A-C

254th National Meeting (2017)

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