A New Approach to Sesquiterpene Arenes of the 9,11‐Drimenyl Type (= [(1E,2RS,4aRS,8aRS)‐Octahydro‐2,5,5,8a‐tetramethylnaphthalen‐1(2H)‐ylidene] methyl Type)

A new reaction sequence for the synthesis of the sesquiterpene arenes (±)‐wiedendiol B ((±)‐1) and the siphonodictyal B derivative (±)‐ 21 consists in the coupling of (±)‐drimanoyl chloride ((±)‐3) with lithiated and appropriately substituted aromatic synthons to furnish the ketones (±)‐7 and (±)‐17 which were reduced to the benzyl alcohols (±)‐8a,b and (±)‐18a,b, respectively (Schemes 5, 4, and 12). The 9,11‐double bond of the drimenes (±)‐9 and (±)‐19 was formed by elimination of H2O from the benzyl alcohols (±)‐8a,b and (±)‐18a,b (Schemes 6 and 12). New alternatives were applied to this elimination reaction involving either the pyridine ⋅ SO3 complex or chloral as reagents.