ChemInform Abstract: Cascade Enantioselective Synthesis of 3‐Arylphthalides Using Chiral Auxiliary Route.

Abstract

Route. -An enantioselective synthesis of 3-arylphthalides (II) is achieved using (S)-phenylethylamine as a chiral auxiliary. Reduction of chiral ketoamides (I) followed by acid-catalyzed lactonization affords title compounds (II) in 75-85% enantioselectivity. -(KARNIK*, A. V.; KAMATH, S. S.; Synthesis 2008, 12, 1832-1834; Dep. Chem., Univ. Mumbai, Vidyanagari, Mumbai 400 098, India; Eng.) -M. Paetzel 43-116

Studies on synthetic and structural characterization of new fluorine substituted phthalides of pharmaceutical interest

“…28 Although organic compounds with phthalide moieties in their structures are well known as analytical reagents and for their photochromatic properties, during recent years, interest in this area has been regenerated and gained a new momentum due to diverse pharmacological properties associated with these compounds. Phthalide [1-(3H)-isobenzofuranone] structures are present in large member of natural products and biologically active compounds 29,30 . A number of medicinal plants are found to contain various phthalides as their active principles 31 .…”

“…The precise biological activity of 3-substituted phthalides is often crucially related with chirality 30,50 . Chiral 3-substituted phthalides such as isochracinic acid 51 , herbaranic acid 51 , cytosporone E 52 have been found to exhibit antibacterial activity, and fuscinarin 53 is a potent human CCR5 antagonist, effectively blocking HIV entry into host cell.…”