Syntheses in the Isocamphane Series, XXVIII. Analogues of δ-Santalol, II

Article abstract of DOI:10.1007/BF00809933

The synthesis of 3-(3,3-dimethyl-2-exo-norbornyl)-2-methylprop-2-en-1-ol (3) and of 8-hydroxymethyl-8-methylcamphene (4) is described. 3 and 4 are analogues of δ-Santalol (1) with the allylic hydroxyl group in a position of two or three carbon atoms closer to the bicyclic nucleus compared to 1. 4 is also an analogue to Patchenol which is used sometimes to blend the patchouli oil.The odour impression of these compounds, of the pure endo-epimer of 3, and of the endo-exo-mixture of 3 are described and compared with the odour of 1 and a further analogue whose synthesis has already been reported in a preceding paper. - Keywords: Allylic alcohol; Allylic oxidation; Camphene; Camphoraceous odour; 3-(3,3-Dimethyl-2-exo-norbornyl)-2-methylprop-2-en-1-ol; Earthy odour; 8-Hydroxymethyl-8-methylcamphene; Isocamphane derivatives; Methylpatchenol; Osmophoric hydroxyl group; Selenium dioxide; Woody odour