A concise synthesis of marine natural product (-)-15-oxopuupehenol from (+)-sclarelide.

A step-economical synthesis of (-)-15-oxopuupehenol from cheap and readily available (+)-sclarelide is achieved with 20.3% overall yield in 9 steps. The key features of this synthetic mythology include a palladium catalyzed tandem carbine migratory insertion reaction to construct the key skeleton, a DDQ-mediated isomerization/oxidation of allyl alcohol to afford α, β-unsaturated ketone, and a NaOH-induced intramolecular Michael addition followed by acetonide deprotection to give (-)-15-oxopuupehenol.