The mucronatin-class compounds, derived from the plant <i>Tetrapterys mucronata, </i>show promising biological activity. BINOL-derived organocatalytic conjugate addition is a promising synthetic strategy for the total synthesis of these compounds, as well as others containing similar core structures, Discoipyrrole D and cytoblastin. The challenge of indole functionalization was addressed using iridium catalysis. The subsequent formation of an indole trifluoroborate salt allows for the use of (<i>R</i>)-TN1 catalyst, developed previously by our group, to add the indole to an unsaturated aldehyde stereoselectively, completing the core structure.

Progress towards the total synthesis of indole-containing natural products using organocatalytic conjugate addition

255th National Meeting (2018)

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