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A Biomimetic Route to the Peptide Alkaloid Anachelin
Author(s) -
Gademann Karl,
Bethuel Yann
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200453909
Subject(s) - annulation , peptide , natural product , chemistry , catechol , combinatorial chemistry , biogenesis , substrate (aquarium) , biosynthesis , oxidase test , stereochemistry , enzyme , biochemistry , biology , catalysis , gene , ecology
A postulated biogenesis forms the basis for a synthetic route to the natural product anachelin H ( 1 ). Key steps include a tellurium‐mediated, oxidative aza annulation and a Claisen condensation under mild conditions. Experiments with a model substrate indicate that it is likely that a catechol oxidase‐type enzyme is involved in the biosynthesis of the anachelin chromophore.
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