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Iodolactonization

Iodolactonization (or, more generally, Halolactonization) is an organic reaction that forms a ring (the lactone) by the addition of an oxygen and iodine across a carbon-carbon double bond. The reaction was first reported by M. J. Bougalt in 1904 and has since become one of the most effective ways to synthesize lactones. Strengths of the reaction include the mild conditions and incorporation of the versatile iodine atom into the product.

Iodolactonization has been used in the synthesis of many natural products including those with medicinal applications such as vernoplepin and vernomenin, two compounds used in tumor growth inhibition, and vibralactone, a pancreatic lipase inhibitor that has been used in the treatment of obesity. Iodolactonization has also been used by E.J. Corey to synthesize numerous prostaglandins.