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

被引：32

作者：

Fujimoto, S

Yoshikawa, K

Itoh, M

Kitahara, T

机构：

[1] Univ Tokyo, Dept Appl Biol Chem, Grad Sch Agr & Life Sci, Bunkyo Ku, Tokyo 1138657, Japan

[2] T Hasegawa Co Ltd, Tech Res Ctr, Nakahara Ku, Kawasaki, Kanagawa 2110022, Japan

来源：

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2002年 / 66卷 / 06期

关键词：

cyclic ketones; cycloalkanes; metathesis; ruthenium;

D O I：

10.1271/bbb.66.1389

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

(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)-3tert-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).

引用

页码：1389 / 1392

页数：4