Efficient synthesis of karrikinolide via Cu(II)-catalyzed lactonization

The efficient total synthesis of karrikinolide (KAR(1)), a potent plant growth regulator discovered in smoke from burning plant material, is described. 3-Hydroxy-4-pyranone, prepared from D-xylose, was subjected to a Cu(II)-catalyzed transesterification-Wittig lactonization to afford the dihydrofuropyran in good yield. Finally, radical bromination, followed by olefin formation, provided KAR(1) in acceptable yield. (C) 2010 Elsevier Ltd. All rights reserved.