19 research outputs found

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

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    International audienceA 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

    Asymmetric Synthesis of Two Hydroxylated Pyrrolizidines From a <i>C</i>-Allyl Epoxypyrrolidine

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    <div><p></p><p>The efficient two-step preparation of a new pivotal C-allyl epoxypyrrolidine intermediate from an enantio-enriched epoxyaldehyde precursor is described. The synthetic potential of this building block is demonstrated with the first enantioselective synthesis of two hydroxylated pyrrolizidine relying on a regio- and stereocontrolled epoxide opening reaction.</p></div
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