Reductive Radical Cyclizations for Heterocycle Synthesis

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The development of modern and efficient methods for the synthesis of heterocyclic building blocks is of fundamental importance for the synthesis of natural products and drugs as well as industrial applications. The titanium(III)-catalyzed radical cyclizations that will be developed in this project will enable unconventional, flexible, and straightforward syntheses of central indole, pyrrole, indolizidine, and quinolizidine building blocks, as well as multifunctionalized pyridines. In addition, structural fragments such as 3-aminoindoles and 3-pyrroles will become directly available and can be derivatized in situ. Previously, these molecule classes were rarely employed in organic synthesis due to their instability and limited synthetic access. The applicability of the presented innovative cyclization methods will be demonstrated on highly efficient total syntheses of natural products such as isatisin A, mitragynin and mitragynin pseudoindoxyl. The successful completion of this project will further establish the titanium(III)-catalysis as a versatile method for heterocycle synthesis.