Total synthesis 2-epi-α-cedren-3-one via a cobalt-catalysed Pauson-Khand reaction
| Autor: | Mark McLaughlin, Laura C. Paterson, William J. Kerr, Colin M. Pearson |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Annulation
Natural product 010405 organic chemistry Stereochemistry Pauson–Khand reaction Organic Chemistry Total synthesis 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Intramolecular force Drug Discovery Wittig reaction QD Organic synthesis |
| Zdroj: | Tetrahedron. 74:5062-5068 |
| ISSN: | 0040-4020 |
| Popis: | Herein we target the total synthesis of 2-epi-α-cedren-3-one, a natural compound isolated from the essential oil of Juniperus thurifera. Overall, our synthetic sequence presents an optimised and robust series of chemical transformations, with prominent features including a low temperature and highly (Z)-selective Wittig olefination reaction, which is vital for the establishment of the relative stereochemistry within the final natural product, and a microwave-assisted, catalytic, intramolecular Pauson-Khand cyclisation reaction, which is used to construct the intriguing tricyclic core of the target molecule. Our optimum cyclisation protocol utilises only 20 mol% of transition metal, and delivers the complex tricyclic structure in just 10 min. Further manipulations of the annulation product culminate in the first total synthesis of the described natural target. |
| Databáze: | OpenAIRE |
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