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Synthesis, Biosynthesis, and Absolute Configuration of Vioxanthin
Author(s) -
Bode Silke E.,
Drochner Daniel,
Müller Michael
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.200701014
Subject(s) - enantioselective synthesis , absolute configuration , biosynthesis , stereochemistry , stereoselectivity , chemistry , path (computing) , phenol , intermolecular force , computer science , organic chemistry , molecule , enzyme , programming language , catalysis
Seeing double : The biosynthesis (path a) of the biarylic compound vioxanthin ( 1 ) by regio‐ and stereoselective intermolecular oxidative phenol coupling is explored in Penicillium citreoviride and the first enantioselective total synthesis of 1 is described (path b). The absolute configuration of ( P , R , R )‐ 1 and its stereoisomer ( M , R , R )‐ 1 was elucidated by combining synthetic methods and feeding experiments with 13 C‐labeled substrates.