124842-71-3Relevant articles and documents
THE RACEMIC FORM AND THE TWO ENANTIOMERS OF 4-METHYL-1-NONANOL, A SEX ATTRACTANT OF THE YELLOW MEALWORM, Tenebrio molitor L.
Carpita, Adriano,Magistris, Elisabetta De,Rossi, Renzo
, p. 99 - 106 (2007/10/02)
The racemic form of 4-methyl-1-nonanol, (R)(S)-1, a sex attractant secreted by the female of the yellow mealworm, has been synthesized in 31 percent overall yield from commercially available methyl 2-octynoate, 2.Almost enantiomerically pure (R)- and (S)-1 have been stereospecifically synthesized in 21.3 and 23.9 percent overall yields, respectively, starting from methyl hydrogen (R)-3-methylglutarate, (R)-3.A precursor for (S)-1, i.e. (S)-3-methyloctanoic acid, (S)-4, has been also prepared in 84 percent yield and over 96 percent enantiomeric purity by the BF3-mediated 1,4-addition of n-pentylcopper to (-)-8-phenylmenthyl crotonate, 15, followed by saponification.The enantiomeric purities of methyl (R)-3-methyloctanoate, (R)-7, and (S)-3-methyl-1-octanol, (S)-8, have been determined by converting these compounds into (R)- and (S)-3-methyloctanoic acid, (R)-4 and (S)-4, respectively, followed by GLC analysis of the corresponding 1-(1-naphthyl)ethylamides obtained from nearly optically pure (R)-1-(1-naphthyl)ethylamine.
