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Updated: May 28, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Catalytic asymmetric functionalization of inert bonds and synthesis of bioactive natural products
1Ecole polytechnique fédérale de Lausanne, EPFL SB ISIC LCSA, BCH 4305, CH-1015 Lausanne. nicolai.cramer@epfl.ch
Abstract:
The direct and enantioselective functionalization of inert bonds such as carbon-hydrogen and carbon-carbon is an emerging tool towards more sustainable and efficient synthetic methods. The individual activation pathways like concerted deprotonation metalations, directed activations, beta-carbon eliminations or retro-allylations proceed by completely different mechanisms and therefore have complementary requirements and different associated challenges. A careful fine-tuning of the transition-metal complex is critical for each mechanism, but a very broad structural space can be covered as well. These methods enhance the synthetic chemist's toolbox allowing more concise, efficient synthetic routes to be executed in target-oriented synthesis. This is illustrated by the examples of a synthesis of largazole and the core of stachyflin from our group.
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