A Total Synthesis of (−)-Strychnine Using Photoredox Catalysis
Rainer Wiechert, Leander Geske, Jasmin Hammes, Dogus Tuncer, Till Opatz
TL;DR
The paper presents a new and efficient way to synthesize strychnine using light-driven chemical reactions.
Contribution
A novel synthesis route for strychnine using photoredox catalysis and renewable starting materials.
Findings
A photoredox-catalytic C2-cyanomethylation step was successfully used.
A condensation-electrocyclization cascade efficiently linked two fragments.
Photochemical decarboxylation provided access to strychnofluorine.
Abstract
A concise route toward (−)-strychnine is presented. Key steps include the photoredox-catalytic C2-cyanomethylation of Boc-l-Trp-OMe and a condensation-electrocyclization cascade linking two fragments convergently to obtain an advanced intermediate. A photochemical decarboxylation provided convenient access to strychnofluorine, which could be transformed through the Wieland–Gumlich aldehyde to strychnine. All building blocks can be traced back to renewable sources.
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Taxonomy
TopicsPlant-based Medicinal Research · Advanced Synthetic Organic Chemistry · Radical Photochemical Reactions