Tandem Favorskii intermediate/cyclization leading to tricyclo[220.127.116.11] decanediones
Pulmonary Disease, Chronic Obstructive
The mechanism of dehydrobromination of the bromodiketone 8 leading to the unusual ring system of tricyclo[18.104.22.168]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.
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