Synthesis of a dicyano abietane, a key intermediate for the anti-inflammatory agent TBE-31

  • Org Lett. 2014 Jan 3;16(1):322-4. doi: 10.1021/ol403289y.
Evans O Onyango  1 ,  Liangfeng Fu ,  Gordon W Gribble
Affiliations
  • 1. Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
PMID: 24303944 DOI: 10.1021/ol403289y
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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