An efficient approach to dihydrofurocoumarins via palladium-catalyzed annulation of 1,3-dienes by o-iodoacetoxycoumarins.
The palladium-catalyzed annulation of 1,3-dienes by o-iodoacetoxycoumarins provides an efficient method for the synthesis of biologically interesting dihydrofurocoumarins. The presence of the acetyl group on the phenolic oxygen and the use of silver carbonate as a base are crucial for this process. This reaction is very general and regio- and stereoselective, and a wide variety of terminal, cyclic, and internal 1,3-dienes can be utilized. Derivatization of the annulation products provides an efficient approach to numerous analogues of natural products.
Rozhkov
Roman V
RV
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Larock
Richard C
RC
D002254:Carbonates; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010100:Oxygen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D018030:Silver Compounds
D002254:Carbonates; D003374:Coumarins; D005663:Furans; D007202:Indicators and Reagents; D018030:Silver Compounds; D010165:Palladium; D010100:Oxygen; C033260:silver carbonate