183. Synthesis of (±)-hirsutene by a catalytic allylpalladium-alkyne cyclization/carbonylation cascade
     Oppolzer, W.; Robyr, C.
     Tetrahedron 1994, 50, 415-424

The tricyclic terpenoid (±)-hirsutene (1) has been synthesized starting from 2-hydroxy-4,4-dimethyltetrahydropyrane. In the key step, acyclic enynyl carbonate 7 afforded bicyclooctenone 2 via a 85% diastereoselective palladium catalyzed metallo-ene/carbonylation reaction cascade.

DOI : 10.1016/S0040-4020(01)80764-X 

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