Hypervalent iodine(III)-mediated tandem oxidative reactions: application for the synthesis of bioactive polyspirocyclohexa-2,5-dienones

In 2002, we reported the first total syntheses of potent antimalarial natural products, the aculeatins, employing the concept of tandem oxidative reactions mediated by hypervalent iodine(III) reagent to access to polyspirocyclohexa-2,5-dienone cores in very concise manner. Efforts in this field have allowed to identify cyclohexa-2,5-dienone group as a new potent class of pharmacophoric group for treating malaria disease. This article sums up recent contributions devoted to the synthesis of complex and diverse polycyclic structures using the concept of tandem oxidative activations, with p-phenol as co-reactant. More recently, we have explored a variant of the new tandem oxidative reactions that employs a catalytic amount of 4-iodotoluene in the presence of mCPBA as the stoichiometric oxidant (Kita's procedure). (C) 2010 Elsevier Ltd. All rights reserved.