4.1 Article

Catalytic Asymmetric Functionalization of Inert Bonds and Synthesis of Bioactive Natural Products

Journal

CHIMIA
Volume 65, Issue 9, Pages 656-658

Publisher

SWISS CHEMICAL SOC
DOI: 10.2533/chimia.2011.656

Keywords

Asymmetric catalysis; C-C activation; C-H activation; Natural products; Transition metals

Funding

  1. ETH Zurich [ETH-16 08-3]
  2. Swiss National Foundation [21-119750.01]
  3. Fonds der Chemischen Industrie

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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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