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

To investigate lignin degradation, scientists commonly use model compounds. Unfortunately, these models are most of the time simple β- -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...

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Bibliographic Details
Published in:Frontiers in chemistry 2019-12, Vol.7, p.842-842
Main Authors: Flourat, Amandine L, Peru, Aurélien A M, Haudrechy, Arnaud, Renault, Jean-Hugues, Allais, Florent
Format: Article
Language:English
Subjects:
C-C coupling
Chemical Sciences
Chemistry
coniferyl alcohol
lignin models
monolignol
Organic chemistry
total synthesis
trimers
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Summary:To investigate lignin degradation, scientists commonly use model compounds. Unfortunately, these models are most of the time simple β- -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 -possessing side-chains and both robust β-5 bond and labile β- -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 S between a phenolate and a bromoketoester, and (3) a modified Upjohn dihydroxylation or a palladium-catalyzed hydrogenation. (β-5)-(β- -4) dihydroxytrimer and dihydrotrimer of coniferyl alcohol ( ) were obtained in good global yield, 9 and 20%, respectively, over nine steps starting from ferulic acid.
ISSN:2296-2646
2296-2646
DOI:10.3389/fchem.2019.00842