Total synthesis of actinobolin from d-glucose by way of the stereoselective three-component coupling reaction

Total synthesis of (−)-actinobolin starting from d-glucose is described. Stereocontrolled three-component coupling reactions of a cyclohexenone derived from d-glucose by way of Ferrier's carbocyclization, with vinyl cuprate and 2-alkoxypropanal effectively constructed the carbon framework of 3. The formal synthesis of (+)-actinobolin starting from d-glucose was also accomplished.