Total Synthesis of (±)-Eucophylline. A Free-Radical Approach to the Synthesis of the Azabicyclo[3.3.1]nonane Skeleton
| Autor: | Frédéric Robert, Shireen Mohammed, Haitham Hassan, Yannick Landais |
|---|---|
| Přispěvatelé: | Institut des Sciences Moléculaires (ISM), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Université Montesquieu - Bordeaux 4-Institut de Chimie du CNRS (INC), H.H. and S.M. thank respectively the Erasmus-Mundus Green IT program (3772227-1-2012-ES-ERA MUNDUS-EMA21) and the Kurdistan government (HCDP program) for PhD grants. ANR (MCR-RAD, 11-BS07-010-01) and CNRS are gratefully acknowledged for financial support. We thank Prof. L. Ghosez (IECB, University of Bordeaux) and Prof. J. Lebreton (University of Nantes) for helpful discussions and Mr. M. A. Jean (University of Bordeaux) for preliminary experiments. M. Stéphane Massip (IECB, University of Bordeaux) is acknowledged for X-ray diffraction studies. |
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
Magnetic Resonance Spectroscopy
Free Radicals Stereochemistry [SDV]Life Sciences [q-bio] MESH: Molecular Structure Alkenes 010402 general chemistry 01 natural sciences Biochemistry Coupling reaction Amidine chemistry.chemical_compound MESH: Apocynaceae MESH: Free Radicals Alkanes [CHIM]Chemical Sciences Physical and Theoretical Chemistry MESH: Cyclization Olefin fiber Azabicyclo Compounds Bicyclic molecule Molecular Structure 010405 organic chemistry MESH: Magnetic Resonance Spectroscopy Organic Chemistry Total synthesis Stereoisomerism MESH: Stereoisomerism 0104 chemical sciences 3. Good health Apocynaceae MESH: Alkanes Benzonitrile chemistry Cyclization Nonane MESH: Azabicyclo Compounds |
| Zdroj: | Organic Letters Organic Letters, American Chemical Society, 2015, 17 (18), pp.4518-4521. ⟨10.1021/acs.orglett.5b02218⟩ |
| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/acs.orglett.5b02218⟩ |
| Popis: | International audience; The first total synthesis of eucophylline was reported in 10 steps and 10% overall yield. The naphthyridine core of eucophylline was prepared through the coupling between a strained azabicyclo[3.3.1]nonan-2-one and a trisubstituted benzonitrile, followed by a cyclization of the corresponding amidine. This coupling reaction was shown to proceed through a stable bicyclic chloroenamine intermediate. The azabicyclo[3.3.1]nonan-2-one skeleton was in turn accessible through a straightforward sequence including a free-radical three-component olefin carbo-oximation as a key step. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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