Improved stereoselective synthesis of optically active methylene lactone, key intermediate for the synthesis of 1,2-oxidized furofuran lignan, by direct alpha-methylenation to butanolide.
(3R)-3-[(1R)-1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-4,5-methylenedioxyphenyl) methyl]-2-methylene-4-butanolide, which is a key intermediate for the synthesis of 1,2-oxidized furofuran lignan, was stereoselectively synthesized from L-glutamic acid by applying direct methylenation to butanolide.
Yamauchi
S
S
College of Agriculture, Ehime University, Matsuyama, Japan. syamauch@agr.ehime-u.ac.jp
Yamamoto
N
N
Kinoshita
Y
Y
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D004149:Dioxoles / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D006838:Hydrocarbons; D017705:Lignans / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
C420223:3-(1-(tert-butyldimethylsilyl)oxy-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl)-2-methylene-4-butanolide; D004149:Dioxoles; D005663:Furans; D006838:Hydrocarbons; D017705:Lignans; C030011:carbene; D015107:4-Butyrolactone; D008697:Methane; C039281:furan