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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...
The Lewis acid-promoted rearrangement of two 10-methyl-4,5-epoxydecalins bearing a trimethylsilyl (TMS) group on C-1 or C-9 has been studied. Migration of the C-9 methylene group to C-5 is the major reaction pathway when the TMS and the oxirane groups are on the same ring while methyl migration results exclusively when they are on different rings.
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