Tandem Favorskii Intermediate/Cyclization Leading to Tricyclo[4.4.0.0]decanediones |
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| Authors: | Sasan Karimi Julia Christodoulou Gopal Subramaniam |
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| Institution: | 1. Department of Chemistry , Queensborough Community College/CUNY , Bayside, New York, USA skarimi@qcc.cuny.edu;3. Department of Chemistry and Biochemistry , Queens College/CUNY, Flushing , New York, USA |
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| Abstract: | The mechanism of dehydrobromination of the bromodiketone 8 leading to the unusual ring system of tricyclo4.4.0.0]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. |
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| Keywords: | Copaene Favorskii intermediate Ylangene |
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