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

O. Stephen Ojo, Brunello Nardone, Stefania F. Musolino, Andrew R. Neal, Liam Wilson, Tomas Lebl, Alexandra M.Z. Slawin, David B. Cordes, James E. Taylor, James H. Naismith, Andrew D. Smith, Nicholas J. Westwood

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)266-273
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number2
Early online date1 Dec 2017
DOIs
Publication statusPublished - 14 Jan 2018

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics'. Together they form a unique fingerprint.

Cite this