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A Concise Synthesis of Lentiginosine Derivatives Using a Pyridinium Formation via the Mitsunobu Reaction

Abstract : A four-step synthesis of (−)-lentiginosine and its epimers is described starting from 2-bromopyridine. The key step consisted of a quaternarization of a fully unprotected pyridinium-polyol unit using Mitsunobu methodology. Subsequent PtO2-catalyzed diastereoselective hydrogenation of the pyridinium ring proceeded smoothly and led to the expected dihydroxyindolizidines with excellent yields. This stereochemically flexible strategy has been illustrated by the concise total synthesis of non-natural products derivatives such as (−)-lentiginosine and its stereoisomers in high yields.
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Submitted on : Thursday, November 28, 2019 - 3:59:49 PM
Last modification on : Thursday, July 2, 2020 - 3:29:42 AM

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Rabah Azzouz, Corinne Fruit, Laurent Bischoff, Francis Marsais. A Concise Synthesis of Lentiginosine Derivatives Using a Pyridinium Formation via the Mitsunobu Reaction. Journal of Organic Chemistry, American Chemical Society, 2008, 73 (3), pp.1154-1157. ⟨10.1021/jo702141b⟩. ⟨hal-02385007⟩

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