Journal of Organic Chemistry p. 2862 - 2866 (1993)
Update date:2022-08-05
Topics:
Delgado, Antonio
Clardy, Jon
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.
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