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

ABSTRACT: To investigate lignin degradation, scientists commonly use model compounds. Unfortunately, these models are most of the time simple ?-O-4 dimers and do not sufficiently mimic the wide complexity of lignin structure (i.e., aliphatic side chains and robust C-C 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 ?-5 bond and labile ?-O-4 bond-via a chemo-enzymatic pathway. Key steps were (1) the C-C coupling via laccase-mediated oxidation, (2) the C-O coupling via a simple SN2 between a phenolate and a bromoketoester, and (3) a modified Upjohn dihydroxylation or a palladium-catalyzed hydrogenation. (?-5)-(?-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.

SUBMITTER: Flourat AL 

PROVIDER: S-EPMC6913187 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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

Flourat Amandine L AL   Peru Aurélien A M AAM   Haudrechy Arnaud A   Renault Jean-Hugues JH   Allais Florent F  

Frontiers in chemistry 20191209

To investigate lignin degradation, scientists commonly use model compounds. Unfortunately, these models are most of the time simple β-<i>O</i>-4 dimers and do not sufficiently mimic the wide complexity of lignin structure (i.e., aliphatic side chains and robust C-C bonds). Herein, we present a methodology to access advanced lignin models through the first synthesis of two trimers of monolignol <b>G</b>-possessing side-chains and both robust β-5 bond and labile β-<i>O</i>-4 bond-via a chemo-enzym  ...[more]

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