Synthesis of (±) cis-substituted cyclohexenyl and cyclohexanyl nucleosides via a double Mitsunobu-type reaction

Karine Barral (1) , Philippe Halfon (2) , Gérard Pèpe (1) , Michel Camplo (1)

1 GCOMM - Groupe de chimie organique et matériaux moléculaires
2 GSP - GenoScience Pharma [Marseille]

This letter describes the synthesis of (±) cis -substituted cyclohexenyl and cyclohexanyl nucleosides. The synthesis of cis isomers was successfully achieved by the use of two consecutive Mitsunobu reactions involving an inversion of configuration and a sugar–base condensation.

Domains: Chemical Sciences; Medicinal Chemistry

Karine Barral, Philippe Halfon, Gérard Pèpe, Michel Camplo. Synthesis of (±) cis-substituted cyclohexenyl and cyclohexanyl nucleosides via a double Mitsunobu-type reaction. Tetrahedron Letters, 2002, 43 (1), pp.81-84. ⟨10.1016/S0040-4039(01)02107-4⟩. ⟨hal-02061647⟩