Enantioselective Stereodivergent Synthesis of Jaspine B and 4-epi-Jaspine B from Axially Chiral Allenols

Heba Alnazer , Tessa Castellan (1) , Yahya Salma (2) , Yves Génisson (1) , Stéphanie Ballereau (1)

1 SPCMIB - Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique
2 I2MR - Institut de médecine moléculaire de Rangueil

A short enantioselective synthetic route to the cytotoxic marine natural jaspine B has been developed. A chiral non-racemic primary -allenol, obtained from pentadecanal, gave access to an enantioenriched 2-tetradecyl-2,5-dihydrofuran as key intermediate. A stereodivergent functionalization of this dihydrofuran allowed access in few steps to jaspine B and its 4-epimer.

Mots clés: jaspine B; pachastrissamine; allenol; enatioselective allenylation; epoxydation; jaspine B

Domaines: Chimie

Heba Alnazer, Tessa Castellan, Yahya Salma, Yves Génisson, Stéphanie Ballereau. Enantioselective Stereodivergent Synthesis of Jaspine B and 4-epi-Jaspine B from Axially Chiral Allenols. SYNLETT, 2019, 30 (02), pp.185-188. ⟨10.1055/s-0037-1610344⟩. ⟨hal-02059333⟩