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Asymmetric Methods for the Synthesis of Flavanones, Chromanones, and Azaflavanones
Author(s) -
Nibbs Antoinette E.,
Scheidt Karl A.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101228
Subject(s) - chemistry , stereocenter , flavanone , epimer , heteroatom , flavones , stereochemistry , stereoselectivity , combinatorial chemistry , organic chemistry , enantioselective synthesis , ring (chemistry) , flavonoid , catalysis , chromatography , antioxidant
Flavanones, chromanones, and related structures are privileged natural products that display a wide variety of biological activities. Although flavanoids are abundant in nature, there are a limited number of available general and efficient synthetic methods for accessing molecules of this class in a stereoselective manner. Their structurally simple architectures belie the difficulties involved in installation and maintenance of the stereogenic configuration at the C2 position, which can be sensitive and can undergo epimerization under mildly acidic, basic, and thermal reaction conditions. This review presents the methods currently used to access these related structures. The synthetic methods include manipulation of the flavone/flavanone core, carbon‐carbon bond formation, and carbon–heteroatom bond formation.