(R,S)-4-Methyl-1-nonanol, (I) was prepd. in 31% overall yield from Me 2-octynoate. Almost enantiomerically pure (R)- and (S)-I have been stereospecifically synthesized in 21.3 and 23.9% overall yields, resp., from (R)-HO2CCH2CHMeCH2CO2Me. (S)-3-Methyloctanoic acid, II has been prepd. in 84% yield and >96% enantiomeric purity by the BF3-mediated 1,4-addn. of 1-pentylcopper to (-)-8-phenylmenthyl crotonate, followed by sapon. The enantiomeric purities of Me (R)-3-methyloctanoate, and (S)-3-methyl-1-octanol, have been detd. by converting these compds. into (R)- and (S)-II, resp., and gas chromatog. anal. of their 1-(1-naphthyl)ethylamides.
The racemic form and the two enantiomers of 4-methyl-1-nonanol, a sex attractant of the yellow mealworm, Tenebrio molitor L
CARPITA, ADRIANO;ROSSI, RENZO
1989-01-01
Abstract
(R,S)-4-Methyl-1-nonanol, (I) was prepd. in 31% overall yield from Me 2-octynoate. Almost enantiomerically pure (R)- and (S)-I have been stereospecifically synthesized in 21.3 and 23.9% overall yields, resp., from (R)-HO2CCH2CHMeCH2CO2Me. (S)-3-Methyloctanoic acid, II has been prepd. in 84% yield and >96% enantiomeric purity by the BF3-mediated 1,4-addn. of 1-pentylcopper to (-)-8-phenylmenthyl crotonate, followed by sapon. The enantiomeric purities of Me (R)-3-methyloctanoate, and (S)-3-methyl-1-octanol, have been detd. by converting these compds. into (R)- and (S)-II, resp., and gas chromatog. anal. of their 1-(1-naphthyl)ethylamides.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
