A mild efficient iodine-catalyzed synthesis of novel anticoagulants with 2,8-dioxabicyclo[3.3.1]nonane core

• Published in: Tetrahedron letters Vol. 54; no. 19; pp. 2386 - 2390
• Main Authors: Ganguly, Nemai C., Mondal, Pallab, Roy, Sushmita
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 08.05.2013; Elsevier
• Subjects: 2,8-Dioxabicyclo[3.3.1]nonane core; Anticoagulants; Chemistry; Chemistry, Organic; Iodine catalyst; Michael-bicycloketalization; Physical Sciences; Science & Technology; Anticoagulants; Michael-bicycloketalization; 2,8-Dioxabicyclo[3.3.1]nonane core; Iodine catalyst; MOLECULAR-IODINE; RAT; WARFARIN; ACETALIZATION; REDUCTASE; CONDENSATION

An efficient coupling of 2-hydroxychalcones/α,β-enones with 4-hydroxycoumarin/5,5-dimethylcyclohexyl-1,3-dione (dimedone) has been accomplished to provide access to a novel class of potential anticoagulants with 2,8-dioxabicyclo[3.3.1]nonane core. The reaction proceeds by Michael-bicycloketalization...