Access to 12-Membered Cyclic ortho,meta-Diarylheptanoids: Total Synthesis of Actinidione via Isomyricanone
| Autor: | Gilles Hanquet, Paul Massé, Sabine Choppin, Françoise Colobert, Lucia Chiummiento |
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| Přispěvatelé: | Laboratoire d'innovation moléculaire et applications (LIMA), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2021 |
| Předmět: |
Natural product
010405 organic chemistry Organic Chemistry Total synthesis 010402 general chemistry Key features 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Ring-closing metathesis chemistry Yield (chemistry) [CHIM]Chemical Sciences Diarylheptanoids Derivative (chemistry) |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2021, 86 (3), pp.3033-3040. ⟨10.1021/acs.joc.0c02489⟩ |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | International audience; We describe herein the first access to 12-membered cyclic [7,0]ortho,meta-diarylheptanoids. The key features of the synthesis include both a Suzuki-Miyaura coupling and a ring closing metathesis. Actinidione, a promising natural product, along with a bioactive tetracyclic derivative were obtained in 14 steps for the first time from cheap commercially available substrates with an overall yield of 18-21%. Our modus operandi complies with the principles of the synthesis ideality by using notably strategic reactions. |
| Databáze: | OpenAIRE |
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