A rearrangement approach to (±)-cerapicol

Article abstract of DOI:10.1016/S0040-4020(99)00258-6

The synthesis and rearrangement of the cyclobutyl methanol 4 is described. The synthesis has been achieved by addition of the Grignard reagent 16 to the bicyclic ketone 22. Experimental procedures for the preparation of both compounds are given. Upon treatment with trifluoroacetic acid and subsequent reduction, 4 yields the norbomanes 24 and 25 and (±)- cerapicol (8). Some consequences concerning the search for other potential precursors of 8 are discussed.