Synthesis of (R)- and (S)- muscone.
(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).
Fujimoto
Satoko
S
Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Japan.
Yoshikawa
Keisuke
K
Itoh
Masamichi
M
Kitaharai
Takeshi
T
D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009812:Odorants; D010476:Perfume / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D003516:Cycloparaffins; D010476:Perfume; C031021:muscone