3 years ago

Metal catalysed versus organocatalysed stereoselective synthesis: The concrete case of myrtucommulones

Metal catalysed versus organocatalysed stereoselective synthesis: The concrete case of myrtucommulones
Myrtucommulones belong to a class of pharmacologically active natural compounds which offer various alternatives to the treatment of pain, inflammation and cancer. Their stereoselective synthesis remains therefore a key-challenge towards its use in the pharmaceutical industry. In the present work myrtucommulone A and B were synthesised through metal catalysis with 81 and 72% ee respectively. Thanks to the use of cinchonidine as an organocatalyst, 82 and 84% de were reached for myrtucommulone A and myrtucommulone F respectively. Simultaneously, a new synthetic method emerged and gave access to new range of possibilities for the preparation of myrtucommulone derivatives under mild conditions or through a one-pot reaction.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017310268

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