Chiral flavanones represent an important class of natural compounds, which are components of tomatoes, citrus fruits like grapefruits, oranges, lemons and some herbs such as mint1 and posses an impressive and varied array of biological and pharmacological properties, namely, anti-inflammatory, immunomodulatory, antiviral and anticarcinogenic activities.2 However, their potential applications as drugs are strongly limited by the expensive extractions from plant tissues that contain them; so their activity has been tested in most cases as racemic mixtures, in spite of the well known relationship between biological properties of chiral compounds and their absolute configuration. In this communication we report the synthesis of some optically active flavanones, based on the asymmetric rhodium-catalyzed conjugate addition of arylboronic acid to chromones,3 in turn prepared by corresponding 2-hydroxy-acetophenones, which can occur with high enantioselectivity.
Synthesis of Chiral Flavanones by Asymmetric Conjugate Addition
SCAFATO, Patrizia;PISANI, LAURA;
2011-01-01
Abstract
Chiral flavanones represent an important class of natural compounds, which are components of tomatoes, citrus fruits like grapefruits, oranges, lemons and some herbs such as mint1 and posses an impressive and varied array of biological and pharmacological properties, namely, anti-inflammatory, immunomodulatory, antiviral and anticarcinogenic activities.2 However, their potential applications as drugs are strongly limited by the expensive extractions from plant tissues that contain them; so their activity has been tested in most cases as racemic mixtures, in spite of the well known relationship between biological properties of chiral compounds and their absolute configuration. In this communication we report the synthesis of some optically active flavanones, based on the asymmetric rhodium-catalyzed conjugate addition of arylboronic acid to chromones,3 in turn prepared by corresponding 2-hydroxy-acetophenones, which can occur with high enantioselectivity.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
