Stereoselective synthesis of eremophilane sesquiterpenoids from β‐pinene
- 1 January 1971
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 90 (9) , 1034-1044
- https://doi.org/10.1002/recl.19710900910
Abstract
2‐Methyl‐4‐isopropylidenecyclohexanone (7) can be obtained in good yield from β‐pinene (2) in a 5‐step sequence. Key step is the acid‐catalysed ring opening of cis‐3‐methylnopinone (5) to give 4‐(l′‐hydroxyisopropyl)‐2‐methylcyclohexanone (6, XOH). Robinson annulation of 7 with trans‐3‐penten‐2‐one proceeds stereoselectively to give α‐vetivone (10). Similar annulation of the isopropenyl isomer (8) affords 7‐epi‐nootkatone (11). 10 can be converted in good yield to nootkatone (13).Keywords
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