Synthesis of (R,S)-muscone from 10-undecenoic acid
作者:
S.Y.Mhaskar,
R.Subbarao,
期刊:
Journal of the American Oil Chemists Society
(Springer Available online 2007)
卷期:
Volume 69,
issue 8
页码: 837-839
ISSN:0003-021X
年代: 2007
DOI:10.1007/BF02635929
出版商: Springer-Verlag-Berlin-Heidelberg
数据来源: Springer
摘要:
Muscone (3-methylcyclopentadecanone) is a major macrocyclic ketone found in the solid secretion, commonly known as musk, from the pouch ofMoschus moschiferus. Herein, we report its synthesis from 10-undecenoic acid, which is the major product of castor oil pyrolysis. Methyl 14-oxotetradecanoate was prepared by radical addition of methyl 10-undecenoate to acrolein. The terminal oxo group was protected as an acetal, and the ester group was treated with the anion of dimethyl methylphosphonate (CH3-(O)P(OMe)2, DMMP) to give 2-(15-dimethoxyphosphynil-14-oxo-pentadecane)-1,3-dioxolane. The acetal protection was removed and the Emmons-Horner reaction was carried out in K2CO3-t-butanol to give 2-cyclopenta-decenone. The addition of MeMgI in the presence of Cu2Cl2gave muscone.
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