The discovery of new synthetic techniques for macrocyclizations is an essential tool in the organic chemist’s toolbox for designing drugs and novel materials. Macrocyclization is defined as a reaction that can create a ring with twelve atoms or more. Macrocycles are found in approximately 20% of all known natural products that contain rings. Relevant examples include antibiotics like valinomycin and gramicidin. While several macrocyclization methods such as Yamaguchi macrolactonization and Grubbs’ ring-closing metathesis reactions are well-known and effective, they rely on sp<sup>2</sup> hybridized carbons to produce the desired macrocycles. The macrocyclization proposed in the presented work has the goal of achieving the first sp<sup>3</sup> hybridized carbon-carbon bond forming macrocyclization. By using metalloid substrates on either end of a chain, activated hypervalent iodine reagents can initiate a transmetallation that affords an iodomacrocycle reactive intermediate. The iodomacrocycle decomposes via reductive elimination to create the macrocycle from a carbon-carbon bond. Our preliminary work for testing the macrocyclization focuses on synthesizing long-chain aliphatic compounds with terminal metalloid groups. Several novel long-chain substrates have been designed and their synthetic routes will be presented. The target compounds have been selected based upon their low volatility and were installed with easily identifiable groups for NMR spectroscopy.

Progress toward methods of macrocyclization via dimetalloid substrates and hypervalent iodine reagents

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ACS Fall 2022

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