4.6 Article

Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 59, Pages 15756-15760

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803785

Keywords

enantiospecific; kinetics; larreatricin; polyphenol oxidase; total synthesis

Funding

  1. Austrian Science Fund (FWF) [P29144]
  2. University of Vienna
  3. Austrian Science Fund (FWF) [P29144] Funding Source: Austrian Science Fund (FWF)

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A concise and efficient total synthesis of the lignan natural product larreatricin as well as an unambiguous assignment of configuration of its enantiomers are reported, resolving a long-held controversy. Enzyme kinetic studies revealed that different polyphenol oxidases show high and remarkably divergent enantioselective recognition of this secondary metabolite.

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