Bicyclo[3.3.1]nonane approach to triquinanes. Formal synthesis of (+/-)Δ(9(12))capnellene and [+/-)Δ(9(12))capnellene-8-β-10α-diol

Article abstract of DOI:10.1016/S0040-4020(01)80453-1

A new synthetic strategy for natural triquinanes is presented as a model study. Stereospecific rearrangement of the ready accessible bicyclo[3.3.1]nonanic acetoxychloride 6 gave the cis-pentalanic hydroxyaldehyde 5, which has been converted into the ketone 4 already reported as a key intermediate in some syntheses of the title capnellenes.