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Enantioselective Syntheses of the Proposed Structures of Kopeolin and Kopeolone

Stephanie Miquet Nicolas Vanthuyne 1 Paul Brémond 2 Gérard Audran 2
1 ChiroSciences
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : The first total syntheses of the proposed structures of kopeolin (1) and kopeolone (3) have been achieved from a common enantiopure chiral building block obtained by a chemoenzymatic enantioconvergent methodology. The syntheses feature two key steps: a one-pot reduction/ diastereoselective protonation followed by a highly diastereoselective addition of an organocerate. The synthetic structures were fully characterized and all stereocenters were confirmed. The results show that the two previously reported structures were not assigned correctly, and suggest an initial structural misassignment during the isolation of the natural products. Thus, two revised structures, 1' for kopeolin and 3' for kopeolone, are proposed.
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Submitted on : Tuesday, February 7, 2017 - 4:43:18 PM
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Stephanie Miquet, Nicolas Vanthuyne, Paul Brémond, Gérard Audran. Enantioselective Syntheses of the Proposed Structures of Kopeolin and Kopeolone. Chemistry - A European Journal, Wiley-VCH Verlag, 2013, 19 (32), pp.10632--10642. ⟨10.1002/chem.201300711⟩. ⟨hal-01460462⟩



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