Tandem Favorskii intermediate/cyclization leading to tricyclo[22.214.171.124] decanediones
Pulmonary Disease, Chronic Obstructive
The mechanism of dehydrobromination of the bromodiketone 8 leading to the unusual ring system of tricyclo[126.96.36.199]decanediones (9 and 10) is described. An entry into the ring system of the sesquiterpenoid hydrocarbons copaene and ylangene, 8 to 9, is achieved in three steps starting with enone 6. Compound 9 was either derived from a direct internal SN2 cyclization of 8 or the Favorskii intermediate 8a. Formation of compound 10, on the other hand, can only occur via the Favorskii intermediate 8a. Structure assignments of 9 and 10 were determined using both one- and two-dimensional NMR experiments. Copyright © Taylor & Francis Group, LLC.
Digital Object Identifier (DOI)
Additional Document Info
has global citation frequency