Dramatic influence of the substitution of alkylidene-5H-furan-2-ones in Diels–Alder cycloadditions with o-quinonedimethide as diene partner: en route to the CDEF polycyclic ring system of lactonamycin
| Autor: | Romain Blanc, Jérôme Thibonnet, Sébastien Dubois, Virginie Héran, Jean-Luc Parrain, Raphaël Rahmani, Fabien Rodier, Laurent Commeiras |
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| Přispěvatelé: | STeRéO, Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Physicochimie des matériaux et des biomolécules (PCMB - EA4244), Faculté des sciences et techniques de Tours, Université François Rabelais, Département de Chimie, Laboratoire PCMB, 32 Avenue Monge, 37200 Tours, France, Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2012 |
| Předmět: |
Indoles
Alkylation Diene Stereochemistry Spironolactone 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry chemistry.chemical_compound Lactonamycine Spirolactone Furan Moiety Physical and Theoretical Chemistry Chemoselectivity Furans Molecular Structure [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Organic Chemistry Quinones Stereoisomerism Cycloaddition 0104 chemical sciences chemistry Cyclization Intramolecular force diels-alder ortho-quinodimethane Naphthoquinones |
| Zdroj: | Organic & Biomolecular Chemistry Organic & Biomolecular Chemistry, 2012, 10, pp.4712-4719. ⟨10.1039/c2ob25299f⟩ Organic and Biomolecular Chemistry Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2012, 10, pp.4712-4719. ⟨10.1039/c2ob25299f⟩ |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c2ob25299f |
| Popis: | International audience; An efficient and rapid synthesis of the CDEF ring system of lactonamycinone is reported via a highly chemo- and diastereoselective intermolecular Diels-Alder cycloaddition between trans-1,2- disilyloxybenzocyclobutene and the appropriate γ-alkylidenebutenolide. The feasibility and the total chemoselectivity of the [4 + 2] cycloaddition for the construction of a spirolactone moiety via an intramolecular approach (IMDA) using both partners is also described demonstrating the versatility of the γ-alkylidenebutenolide building block. |
| Databáze: | OpenAIRE |
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