Total Synthesis of (-)-Ovatolide

Article abstract of DOI:10.1021/jo00062a034

The total synthesis of (-)-ovatolide (1), a tetracyclic indole-containing β-glucosyl derivative with an unusual pyrano<2,3-b>dioxocan-6-one system, is described.The β-glucosidic linkage arose from regio- and stereocontrolled reaction of a protected 1,2-epoxyglucal derivative with 4-hydroxy-5-(benzyloxy)indole, and a lactonization reaction afforded the central dioxocanone system.An alternative strategy that afforded the tetracyclic framework as a mixture of epimers is also described.