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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

Abstract : 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.
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Submitted on : Saturday, September 28, 2013 - 7:00:07 AM
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Sébastien Dubois, Fabien Rodier, Romain Blanc, Raphaël Rahmani, Virginie Héran, et al.. 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. Organic & Biomolecular Chemistry, Royal Society of Chemistry, 2012, 10, pp.4712-4719. ⟨10.1039/c2ob25299f⟩. ⟨hal-00736663⟩

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