Synthesis and Odor of Chiral Partial Structures of Khusimone. Part 1

Abstract

Khusimone (1), one of the main odor‐donating compounds of vetiver oil is subject of the following study on structure/odor relationship. The omittance of the ethano bridge of the tricyclic khusimone leads to a bicyclic system. The stereoselective approach to this degraded structure is described, and the olfactory properties are studied. The key step of the synthesis of the hydrindane nucleus is based on a highly diastereoselective conjugate addition to a chiral oxo‐cyclopentene‐2‐carboxylate.

Odds and Trends: Recent Developments in the Chemistry of Odorants

“…(153) the key odorant of vetiver oil, [87] together with the 2-acetyl-4a-methyl-8-methyleneoctaline 156, which has a powerful woody-amber odor, and nordihydro-b-vetivone 157, which has a strong rich, woody-peppery odor. (À)-160 smelled weakly camphoraceous with a woody by-note, [91] while (À)-162 was camphoraceous with a sweet-herbal by-note, and (À)-163 cedarwoodlike. The odor of the naturally occurring (À)-153 was evaluated by Dragoco perfumers and found to be quinolinelike, reminiscent of cassis and grapefruit, while ()-153 exhibited an unpleasant cresolic, medicinal note.…”

“…In ªDolce vitaº (C. Dior, 1995) overdoses of around 15 % of Majantol (95) and 6 % of Mayol (96) have been combined to harmonize the different floral parts, and to convey smoothness to the fragrance. Florol (97) was often used in combination with hydroxycitronellal (91) and Lilial (94) in muguet accords. Some examples are summarized in Table 2.…”

Design, Synthesis and Structure-Odor Correlation of Novel Spiro[4.5]-decan-2-ones

“…6 Besides, they considered the zizaenone 5 close to but weaker than khusimone (2), and reported eremophiladienal (6) and the new 1,7-cyclogerma-1(10),4-dien-15-al (7) 11 as valuable, typical vetiver-type odorants reminiscent of khusimone (2). However, the norsesquiterpene khusimone (2), present in about 2%, 6 is the only constituent on which both perfumers and chemists agree to possess a typical vetiver odor, and thus also served as the lead in a recent structureodor relationship study of Spreitzer et al [12][13][14]…”

Allerlei Trends: die neuesten Entwicklungen in der Riechstoffchemie

“…Für Khusimon 159 wurde sogar eine technisch gangbare Partialsynthese ausgehend von Vetivensäure ausgearbeitet, [85] aber 159 wurde (noch) nicht in die Parfümerie eingeführt. (À)-160 roch schwach campherartig mit einer holzigen Nebennote, [91] während (À)-162 campherartig mit einer süû-kräuterartigen Nebennote war und (À)-163 zedernholzartig. [87] Mookherjee et al beschrieben die Verbindungen 154 und 155 von Maurer als schwach, grün, wurzelartig und holzig.…”