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Formation of the Pyridazine Natural Product Azamerone by Biosynthetic Rearrangement of an Aryl Diazoketone
Author(s) -
Winter Jaclyn M.,
Jansma Ariane L.,
Handel Tracy M.,
Moore Bradley S.
Publication year - 2009
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.200805140
Subject(s) - pyridazine , diazo , aryl , natural product , biosynthesis , chemistry , stereochemistry , molecule , oxidative phosphorylation , organic chemistry , biochemistry , enzyme , alkyl
All in the family : Knowledge of the biosynthesis of NN containing natural products is limited. Feeding experiments with 13 C and 15 N‐labeled molecules establish that the phthalazinone core of azamerone is derived from the diazo chlorinated meroterpenoid SF2415A3. A biosynthetic mechanism involving an oxidative rearrangement of the aryl diazoketone followed by rearomatization with the dinitrogen group is proposed.