Enantioselectivity in Odor Perception : Synthesis and Olfactory Properties of the New Tricyclic Sandalwood Odorant Fleursandol®

✍ Scribed by Bernd Hölscher; Norbert A. Braun; Berthold Weber; Claus-Hermann Kappey; Manfred Meier; Wilhelm Pickenhagen

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: German
• Weight: 339 KB
• Volume: 87
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200490151

✦ Synopsis

Abstract

The 3‐methyl‐4‐(tricyclo[5.2.1.0^2,6^]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‐2__H__‐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 (2__S__,3__R__,4__E__,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~2~O.