title: Synthesis of (R)- and (S)- muscone.
abstract: (R)-(-)-Muscone (3-methylcyclopentadecanone, 1) the key perfumery component isolated from the male musk deer, Moschus moschiferus,* was synthesized from the easily available chiral building block, (R)-3-tert-butoxycarbonyl-2-methylpropanoic acid (2), by employing ring-closing olefin metathesis (RCM). Antipode (+)-1 was also synthesized in a similar manner from tert-butyl (S)-3-methoxycarbonylbutanoate (10). *(a) Walbaum, H. J. J. Prakt. Chem., 73, 488 (1906); (b) Ruzicka, L., Further considerations on the constitution of muscone. Helv. Chim. Acta, 9, 715, 1008-1017 (1926).
authors.affiliation: Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Japan.
authors.forename: Satoko
authors.initials: S
authors.lastname: Fujimoto
authors.forename: Keisuke
authors.initials: K
authors.lastname: Yoshikawa
authors.forename: Masamichi
authors.initials: M
authors.lastname: Itoh
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kitaharai
mesh_terms: D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009812:Odorants; D010476:Perfume / Q000737:chemistry; D013055:Spectrophotometry, Infrared
chemical_list: D003516:Cycloparaffins; D010476:Perfume; C031021:muscone