871228-11-4Relevant articles and documents
Silicon guided rearrangement of epoxydecalines to spirocyclic compounds. Synthesis of gleenol and axenol from carvone
Blay, Gonzalo,Collado, Ana M.,García, Bego?a,Pedro, José R.
, p. 10853 - 10860 (2007/10/03)
The synthesis of the spirocyclic sesquiterpenes (-)-gleenol and (-)-axenol in enantiomerically pure form has been achieved starting from R-(-)-carvone. The key step is the silicon guided acid-promoted rearrangement of a 9-trimethylsilyl-5,6-epoxy-noreudesmane prepared from 3- trimethylsilyldihydrocarvone in several steps involving Robinson annulation, enone deconjugation and epoxidation. Acid treatment of the epoxy-noreudesmane gave a norspiroaxane as the main product, which was used as intermediate for the synthesis of two naturally occurring sesquiterpenes gleenol and axenol.