First Total Synthesis of (β-5)-(β-O-4) Dihydroxytrimer and Dihydrotrimer of Coniferyl Alcohol (G): Advanced Lignin Model Compounds - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Frontiers in Chemistry Année : 2019

First Total Synthesis of (β-5)-(β-O-4) Dihydroxytrimer and Dihydrotrimer of Coniferyl Alcohol (G): Advanced Lignin Model Compounds

Résumé

To investigate lignin degradation, scientists commonly use model compounds. Unfortunately, these models are most of the time simple β-O-4 dimers and do not sufficiently mimic the wide complexity of lignin structure (i.e., aliphatic side chains and robust CC bonds). Herein, we present a methodology to access advanced lignin models through the first synthesis of two trimers of monolignol G-possessing side-chains and both robust β-5 bond and labile β-O-4 bond-via a chemo-enzymatic pathway. Key steps were (1) the CC coupling via laccase-mediated oxidation, (2) the CO coupling via a simple S N2 between a phenolate and a bromoketoester, and (3) a modified Upjohn dihydroxylation or a palladium-catalyzed hydrogenation. (β-5)-(β-O-4) dihydroxytrimer and dihydrotrimer of coniferyl alcohol (G) were obtained in good global yield, 9 and 20%, respectively, over nine steps starting from ferulic acid.
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Dates et versions

hal-02400612 , version 1 (09-12-2019)

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Amandine Flourat, Aurélien a M Peru, Arnaud Haudrechy, Jean-Hugues Renault, Florent Allais. First Total Synthesis of (β-5)-(β-O-4) Dihydroxytrimer and Dihydrotrimer of Coniferyl Alcohol (G): Advanced Lignin Model Compounds. Frontiers in Chemistry, 2019, 7, pp.842. ⟨10.3389/fchem.2019.00842⟩. ⟨hal-02400612⟩
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