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Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics

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Abstract

Alternative sources of potential feedstock chemicals are of increasing importance as the availability of oil decreases. The biopolymer lignin is viewed as a source of useful mono-aromatic compounds as exemplified by the industrial scale production of vanillin from this biomass. Alternative lignin-derived aromatics are available in pure form but to date examples of the use of these types of compounds are rare. Here we address this issue by reporting the conversion of an aromatic keto-alcohol to the anti- and syn-isomers of Descurainolide A. The key step involves a rhodium-catalyzed allylic substitution reaction. Enantio-enriched allylic alcohols were generated via an isothiourea-catalyzed kinetic resolution enabling access to both the (2R,3R) and (2S,3S) enantiomers of anti-Descurainolide A. In addition we show that the lignin-derived keto-alcohols can be converted into unnatural amino acid derivatives of tyrosine. Finally, these amino acids were incorporated into cyclic peptide scaffolds through the use of both chemical and an enzyme-mediated macrocylisation.

Graphical abstract: Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics

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Publication details

The article was received on 02 Nov 2017, accepted on 01 Dec 2017 and first published on 01 Dec 2017


Article type: Paper
DOI: 10.1039/C7OB02697H
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics

    O. S. Ojo, B. Nardone, S. F. Musolino, A. R. Neal, L. Wilson, T. Lebl, A. M. Z. Slawin, D. B. Cordes, J. E. Taylor, J. H. Naismith, A. D. Smith and N. J. Westwood, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02697H

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