Enantioselcctivity in Odor Perception Synthesis and Olfactory Properties of the New Tricyclic Sandalwood Odorant Fleursandol~R

摘要

The 3-methyl-4-(tricyclo[5.2.1.1,0]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]dec-4-en-8-ones 17 and ent-71a 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'R7'R)-isomer ent-10a is by far the most important representative,with an odor threshold of 5 mug/1 in H_2O.