Synthesis of Lignin Model Compounds

  • ChemPubSoc Europe Logo
  • Author: Ruben Ragg
  • Published Date: 31 August 2016
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Synthesis of Lignin Model Compounds

Related Societies

Paper is one of the most widely used industrial products. However, the main byproduct of the paper fabrication process, the polyphenolic macromolecule lignin, is not often used in industrial processes due to its structural heterogeneity. The most common native substructure in lignin is the so-called β-O-4 unit (roughly 50–65 %, pictured). It could be a valuable target in the cleavage of the lignin macromolecules during biorefinery processes. However, the reactivity of β-O-4 units remains poorly understood.


Joseph J. Bozell, University of Tennessee, Knoxville, USA, and colleagues have developed an enantioselective synthesis of (R,R)-, (S,S)-, (R,S)-, and (S,R)-β-O-4 lignin dimer models. The team used an Evans chiral aldol reaction and a subsequent Mitsunobu inversion with excellent ee (> 99 %) and high overall yields. The reaction could be scaled up to provide multigram quantities. The researchers extended the method to perform the first synthesis of an enantiomerically pure lignin trimer.


These model compounds could help to understand the influence of stereochemistry on the chemical, enzymatic, and microbial degradation of lignin.


 

Article Views: 2554

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH