Heterocycles via C–H functionalization strategies; synthesis of pyrroloindoles and tanshinone IIA

Tucker, Simon Nathan (2022) Heterocycles via C–H functionalization strategies; synthesis of pyrroloindoles and tanshinone IIA. Masters thesis, Memorial University of Newfoundland.

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Abstract

This thesis is divided into two projects. Chapter one discusses the development of tandem C–H functionalization and Michael-type annulation using α-diazocarbonyl compounds for the synthesis of fused indole ring systems. Highlights include the use of cheap copper catalysts, high stereoselectivity, and a robust substrate scope showcasing the amenability of the transformation to various indole and diazo substrates. Details of an interesting base-catalyzed olefin isomerization will also be discussed. Chapter two details a newly developed total synthesis of tanshinone IIA, an abietane diterpenoid from the tanshinone family of natural products. This route is highlighted by access to complex coupling partners through multigram scale reactions starting from simple commercially available starting materials. Key transformations include an iridium-catalyzed borylation, a directed metalation/iodination, and a Brook-type rearrangement to furnish a synthetically challenging ortho-quinone ring. Chapter three presents a summary of this thesis work and potential avenues for future research.

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