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On the Origin of the Haouamine Alkaloids
Author(s) -
Burns Noah Z.,
Baran Phil S.
Publication year - 2007
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.200704576
Subject(s) - biosynthesis , enantioselective synthesis , pyridine , stereochemistry , phenylalanine , chemistry , absolute configuration , biochemistry , organic chemistry , enzyme , amino acid , catalysis
Not what it seemed : Careful reinvestigation of the classic Chichibabin pyridine synthesis has provided evidence against a spontaneous tetramerization pathway in the biosynthesis of the haouamine alkaloids. A simple enantioselective synthesis of haouamine A has illuminated its absolute configuration and points towards a phenylalanine‐based biosynthesis.