6533b7cffe1ef96bd1258cf4
RESEARCH PRODUCT
Silicon guided rearrangement of epoxydecalines to spirocyclic compounds. Synthesis of gleenol and axenol from carvone
Gonzalo BlayJosé R. PedroBegoña GarcíaAna M. Colladosubject
CarvoneSiliconStereochemistryOrganic Chemistrychemistry.chemical_elementCarbocationBiochemistrychemistry.chemical_compoundchemistryDrug DiscoveryRobinson annulationOrganic chemistryAcid treatmentEnonedescription
Abstract 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2005-11-01 | Tetrahedron |