A modular total synthesis of (±)-trigonoliimine CElectronic supplementary information (ESI) available: Characterization data and spectra of new compounds. See DOI: 10.1039/c3cc45512b

A convergent total synthesis of trigonoliimine C has been executed by employing three catalytic transformations in sequence. The key reactions that have been developed in this context include the [Au]-catalyzed addition of protected tryptamine to isatogens and the reduction of N-OH to NH with hydrazine monohydrate. Trigonoliimine C and its analogues have been assembled from simple building blocks by employing three [metal]-catalysed reactions in sequence involving the synthesis of the pentacyclic core.