501929-84-6Relevant articles and documents
Enantioselectivity in odor perception synthesis and olfactory properties of the new tricyclic sandalwood odorant Fleursandol
Hoelscher, Bernd,Braun, Norbert A.,Weber, Berthold,Kappey, Claus-Hermann,Meier, Manfred,Pickenhagen, Wilhelm
, p. 1666 - 1680 (2004)
The 3-methyl-4-(tricyclo[5.2.1.02,6]dec-4-en-8-ylidene)butan-2- ols (=Fleursandol; rac-10), a new class of sandalwood odorants, were synthesized in their enantiomerically pure forms by use of tricyclo[5.2.1.0 2,6]dec-4-en-8-ones 17 and ent-17 and (tetrahydro-2H-pyran-2-yl)- protected 4-bromo-3-methylbutan-2-ols 22 and ent-22 as starting materials (Schemes 2-4). Only four of 16 possible stereoisomers of rac-10 possess the typical, very pleasant, long-lasting sandalwood odor (Table 1). The (2S,3R,4E,1′R,2′R,6′R,7′R)-isomer ent-10a is by far the most important representative, with an odor threshold of 5 μg/l in H 2O.
