largazole and stachyflin

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.

Topics: Biological Products; Catalysis; Depsipeptides; Hydrogen Bonding; Molecular Structure; Sesquiterpenes; Stereoisomerism; Thiazoles