Synthesis of (R)- and (S)- Muscone | Zendy

Satoko Fujimoto | Zendy; Keisuke Yoshikawa | Zendy; Masamichi Itoh | Zendy; Takeshi KITAHARA | Zendy

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Synthesis of (R)- and (S)- Muscone

Author(s) -

Satoko Fujimoto,

Keisuke Yoshikawa,

Masamichi Itoh,

Takeshi KITAHARA

Publication year - 2002

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.66.1389

Subject(s) - olefin metathesis , stereochemistry , metathesis , chemistry , humanities , art , organic chemistry , polymerization , polymer

(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).

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