Organic Letters · 2019 · 11 citations · 20 references
Natural SciencesChemistryMedicinal ChemistryCatalysisNatural Product BiosynthesisOrganic ChemistryCross-coupling ReactionsDiversity-oriented SynthesisHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisTerpenoid BiosynthesisAsymmetric Heterocycle SynthesisAsymmetric SynthesisCyclopropanation ReactionsHeterocycle FunctionalizationPalladium-catalyzed Cross-couplingRing-forming Reactions
Enantioselective synthesis of a highly versatile building block en route to trachylobanes and related terpenoids is presented. The synthesis features diastereoselective Diels-Alder cycloaddition reaction, a cyclopropanation/homoquadricyclane rearrangement cascade, and palladium-catalyzed C-H acetoxylation. The targeted tricyclooctane was obtained in 20% yield over 8 steps and in 95% ee. The ketone and alcohol functional groups serve as handles for further elaboration.
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