New macrocyclic musk compounds

Chem Biodivers. 2004 Dec;1(12):1985-91. doi: 10.1002/cbdv.200490152.


The syntheses and olfactory evaluations of eight new macrocyclic musks with a 1,6-dioxa structure (1a-d and 1'a-d) as well as of twelve optically active 3-methyl macrolides (5a-c and 5'a-c) are reported. These macrocycles were synthesized via intramolecular metathesis mediated by the Grubbs catalyst. Despite the absence of a C=O function, the 1,6-dioxa compounds, both unsaturated (1) and saturated (1'), possess musky odors similar to those of macrocyclic ketones and lactones. Especially 16-membered rings were found to display an intense and pleasant musk character. However, in the case of optically active 3-methyl macrolides (5, 5'), only the (R)-configured 15- and 16-membered rings had intense and pleasant musk notes.

MeSH terms

  • Fatty Acids, Monounsaturated / chemical synthesis*
  • Fatty Acids, Monounsaturated / chemistry
  • Macrocyclic Compounds / chemical synthesis
  • Macrocyclic Compounds / chemistry
  • Odorants*


  • Fatty Acids, Monounsaturated
  • Macrocyclic Compounds
  • musk