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Enantioselective access to a versatile 4-oxazolidinonecarbaldehyde and application to the synthesis of a cytotoxic jaspine B truncated analogue

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Génisson, Yves | Lamandé, Lydia | Salma, Yahya | Andrieu-Abadie, Nathalie | André, Chantal | Baltas, Michel

Edité par CCSD ; Elsevier -

International audience.

The preparation of the versatile aldehyde 15 via a concise route based on a formal anti-asymmetric aminohydroxylation and its use in a 5-step synthesis of a cytotoxic C 12 analogue of the natural anhydrophytosphingosine jaspine B is presented.

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Corrigendum to ‘Single- and double-chained truncated jaspine B analogues: asymmetric synthesis, biological evaluation and theoretical study of an unexpected 5-endo-dig process’ [Tetrahedron 67 (2011) 4253–4262]

Archive ouverte | Salma, Yahya | CCSD

International audience. not available

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 ...

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