Abstract
The transannular cyclopropanation of a keto carbene generated by Rh 2 (OAc) 4 catalysis on a bicyclic dihydropyran nucleus provided a key oxatricyclic ketone intermediate for the synthesis of the [6.6] spirocyclic ring construction. Selective fragmentation of the cyclopropane followed by hydrolytic cleavage of the C−O bond provided the spirocyclic skeleton. Functional group manipulations to adjust oxidation states led to a total synthesis of (±)-β-chamigrene in 14 steps without the use of protection/deprotection schemes
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