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Flexible and enantioselective access to jaspine B and biologically active chain-modified analogues thereof.

Archive ouverte | Salma, Yahya | CCSD

International audience. Whereas the all-cis tetrahydrofuran framework of the cytotoxic anhydrophytosphingosine jaspine B is considered as a relevant pharmacophore, little is known about the influence of the aliphati...

Single- and double-chained truncated jaspine B analogues: asymmetric synthesis, biological evaluation and theoretical study of an unexpected 5-endo-dig process

Archive ouverte | Salma, Yahya | CCSD

International audience. An optimized synthesis of jaspine B analogues bearing an n-octyl or a p-fluorophenethyl lipophilic appendage was developed. Key to the approach was the use of acetylenic nucleophiles for the ...

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

Archive ouverte | Rives, Arnaud | CCSD

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 b...

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