6533b82ffe1ef96bd1295cc7
RESEARCH PRODUCT
Synthesis of toxyloxanthone B
William LewisChristopher J. MoodyChristopher C. NawratDaniele GiallombardoAdam C. NevinRussell R. A. Kitsonsubject
Natural products Xanthones Oxygen heterocycle Benzyne addition Claisen rearrangement.StereochemistryArylOrganic ChemistryRegioselectivitySettore CHIM/06 - Chimica OrganicaRing (chemistry)BiochemistryAryneClaisen rearrangementchemistry.chemical_compoundchemistryPyranDrug DiscoveryXanthonedescription
A synthesis of the naturally occurring xanthone toxyloxanthone B is described, in which the key step is the regioselective addition of a methyl salicylate to a substituted benzyne, followed by cyclization of the intermediate aryl anion to form the xanthone, the regiochemistry of the aryne addition being confirmed by X-ray crystallography. Subsequent introduction of the pyran ring by [3,3]-rearrangement and deprotection completed the synthesis.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-01-01 |