475-23-0Relevant academic research and scientific papers
Structure and Odor, VI. - Preparation and Reactions of Longicamphenilone
Weyerstahl,Peter,Krohn,Kerstin
, p. 1125 - 1128 (2007/10/02)
Longicamphenilone (2) can readily be prepared by phase-transfer-catalysed potassium permanganate oxidation of longifolene (1).The ketone 2 is a convenient starting material for the preparation of the fragrance compounds 3 - 6.
7β-Ethynylnorlongifolane from Carbon Tetrachloride Adduct of Longifolene: Synthesis and Reactions
Dalavoy, V. S.,Deodhar, V. B.,Nayak, U. R.
, p. 5 - 7 (2007/10/02)
Sodium-t-butanol-tetrahydrofuran reagent dechlorinates 3-chloro-7β-chloroethynylnorlongifolane (3) to furnish the novel 7β-ethynylnorlongifolane (4) in 40percent yield; the olefins 5 (30percent) and 6 (7percent) are also formed.Mercuric oxide-catalyzed hydration of 4 gives 7β-acetylnorlongifolane (8) thus fixing the stereochemistry at C-7 in 4.Baeyer-Villiger oxidation/hydrolysis of 8 affords the alcohol (10a) which has been shown to be identical with the carbinol resulting from sodium-n-propanol reduction of C14-ketone (11).Hydroboration-oxidation of 4 generates an aldehyde which on silver oxide oxidation gives homoisolongifolic acid (12).
