The Modular Synthesis and Functionalization of Cyclic Compounds Using Modern Methods

Citation

Lacker, Caitlin Rebecca (2022) The Modular Synthesis and Functionalization of Cyclic Compounds Using Modern Methods. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/61ky-5w83. https://resolver.caltech.edu/CaltechTHESIS:09072021-162545226

Abstract

Accessing libraries of similar compounds quickly is important in the pharmaceutical industry, as it allows for the expedient investigation of a wide variety of parameters. An efficient strategy to access compounds of interest is to start from a single intermediate containing an interesting or pharmaceutically active structure and decorating it with varying functionality to generate a library of related compounds. Cross-coupling is a powerful tool for this type of divergent, modular approach.

Herein, we discuss several strategies geared towards the synthesis of small libraries of compounds of interest. First, a modular approach towards a library of enantioenriched trans cyclobutanes is discussed. This strategy allows for the synthesis of diverse substrates from a single enantioenriched intermediate, and this approach was applied to the synthesis of the small molecule (+)-rumphellaone A. Finally, the development of an enantioselective nickel-catalyzed photoredox cross-coupling to form N-(hetero)benzylic azoles in collaboration with researchers at Merck is discussed.

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