A unified strategy to ent-kauranoid natural products: total syntheses of (-)-trichorabdal A and (-)-longikaurin E
- PMID: 23886049
- DOI: 10.1021/ja406599a
A unified strategy to ent-kauranoid natural products: total syntheses of (-)-trichorabdal A and (-)-longikaurin E
Abstract
The first total syntheses of (-)-trichorabdal A and (-)-longikaurin E are reported. A unified synthetic strategy is employed that relies on a Pd-mediated oxidative cyclization of a silyl ketene acetal to generate an all-carbon quaternary center and build the bicyclo[3.2.1]octane framework. These studies, taken together with our previous synthesis of (-)-maoecrystal Z, demonstrate that three architecturally distinct ent-kauranoids can be prepared from a common spirolactone intermediate.
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