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Highly Regioselective Oxirane Ring‐Opening of a Versatile Epoxypyrrolidine Precursor of New Imino‐Sugar‐Based Sphingolipid Mimics

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Rives, Arnaud | Génisson, Yves | Faugeroux, Vanessa | Zedde, Chantal | Lepetit, Christine | Chauvin, Remi | Saffon, Nathalie | Andrieu-Abadie, Nathalie | Colié, Sandra | Levade, Thierry | Baltas, Michel

Edité par CCSD ; Wiley-VCH Verlag -

International audience. Abstract An in‐depth study of the oxirane ring‐opening reaction of a pivotal epoxypyrrolidine is reported. The introduction of various carbon‐ and heteroatom‐centered nucleophiles at C4 has been achieved with high regiocontrol. The structures of the major products were assigned on the basis on an X‐ray crystallographic study of six examples. A mechanistic study carried out at the B3LYP/6‐31G** level of theory suggested that the steric control of the vinyl substituent was responsible for the regioselectivity. Finally, this approach was used to design and prepare imino‐sugar‐based sphingolipid mimics. A highly cytotoxic C ‐octylpyrrolidine is described. This compound was shown to interfere with the metabolism of sphingolipids in murine melanoma cells, notably in inhibiting the production of glucosylceramide.

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