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Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin
Author(s) -
Martin Harry J.,
Kampatsikas Ioannis,
Oost Rik,
Pretzler Matthias,
AlSayed Emir,
Roller Alexander,
Giester Gerald,
Rompel Annette,
Maulide Nuno
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803785
Subject(s) - enantioselective synthesis , enantiomer , lignan , metabolite , chemistry , stereochemistry , total synthesis , natural product , enzyme , secondary metabolite , organic chemistry , biochemistry , catalysis , gene
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.