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Synthesis of a dicyano abietane, a key intermediate for the anti-inflammatory agent TBE-31
Evans O Onyango1, Liangfeng Fu, Gordon W Gribble
1Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
Abstract:
The synthesis of dicyano abietane 11, a potential precursor to the biologically active tricyclic bis-cyano enone 6 (TBE-31), was accomplished in eight steps from epoxide 13. The synthesis features a Lewis acid promoted stereoselective cyclization of epoxide 13 to generate the tricyclic ring system 12 in one step.
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