Flow Conditions‐Controlled Divergent Oxidative Cyclization of Reticuline‐Type Alkaloids to Aporphine and Morphinandienone Natural Products - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2022

Flow Conditions‐Controlled Divergent Oxidative Cyclization of Reticuline‐Type Alkaloids to Aporphine and Morphinandienone Natural Products

Résumé

Described herein is a divergent continuous-flow approach for the biomimetic oxidative cyclization of reticuline-type alkaloids to aporphine and morphinandienone natural products using hypervalent iodine(III) reagents. The methodologies developed in this work were based on the detailed knowledge of the reaction mechanisms in order to develop robust and original experimental conditions toward the selective synthesis of either aporphine or morphinandienone natural products. In this frame, we exploited the ability of HFIP to stabilize radical cation intermediates and to activate hypervalent iodine(III) oxidants for the flow synthesis of aporphine natural products such as glaucine, rogersine and nantenine. On the other hand, we established that PhI(OAc)(OTf), prepared by action of TMSOTf on PhI(OAc)2, was a powerful oxidant for the synthesis of morphinandienone natural products such as sebiferine and amurine. Also described in this contribution, the very first structure-reactivity relationship to assess the current limits of such oxidative flow processes.

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Chimie
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Dates et versions

hal-03821924 , version 1 (20-10-2022)
hal-03821924 , version 2 (20-03-2023)

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Bi Bali Judicaël Tra, Abollé Abollé, Vincent Coeffard, François‐xavier Felpin. Flow Conditions‐Controlled Divergent Oxidative Cyclization of Reticuline‐Type Alkaloids to Aporphine and Morphinandienone Natural Products. European Journal of Organic Chemistry, 2022, 2022 (22), ⟨10.1002/ejoc.202200301⟩. ⟨hal-03821924v2⟩
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