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Wood Replaces Oil In Chemical Synthesis

Biobased Feedstocks: Researchers carry out natural product syntheses using chemical building blocks derived entirely from wood

by Stephen K. Ritter
November 2, 2015 | A version of this story appeared in Volume 93, Issue 43

An international research consortium has reported its first success in fulfilling a dream of synthesizing chemicals and materials by starting with building blocks derived entirely from wood. Like other chemists, the group led by Anthony J. Arduengo III of the University of Alabama, Tuscaloosa, and Till Opatz of Johannes Gutenberg University Mainz, in Germany, has been looking to use biobased chemicals as a sustainable alternative to nonrenewable fossil resources. The researchers have laid out a strategy, which they call xylochemistry, to source all the organic compounds they need from the resins, oils, and cellulosic biopolymers that trees produce (Angew. Chem. Int. Ed. 2015, DOI: 10.1002/anie.201508500). They demonstrated the approach by carrying out the first total synthesis of a dimeric alkaloid compound called ilicifoline B. The team used wood-derived ferulic acid, methanol, and veratrole to supply all the carbon atoms and the majority of the other atoms needed. The researchers also carried out a total synthesis of the morphine derivative dihydrocodeine. Ilicifoline B has anticancer properties and dihydrocodeine is a painkiller, but Arduengo says the team also aims to prepare compounds for use as automotive coatings, adhesives, and plastics. “Wood is the ideal raw material,” Opatz notes. “Its composition is like a box of varied building blocks from which products for today’s modern world can be manufactured.”

Reaction scheme for converting ferulic acid, veratrole, and methanol to ilicifoline B.


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