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The Synthesis and Configuration of Fukiic Acid Derivatives
- Source :
- Bulletin of the Chemical Society of Japan. 45:1501-1504
- Publication Year :
- 1972
- Publisher :
- The Chemical Society of Japan, 1972.
-
Abstract
- The methylation of 3,4-dimethoxyphenylpyruvic acid (II) gave the corresponding methyl ester (III), which was then subjected to a Wittig reaction with carbomethoxymethylenetriphenylphosphorane to give the corresponding fumaric (IVa) and maleic (IVb) acid derivatives in a 1:3 ratio. The cis-hydroxylation of IVa and IVb with an aqueous solution of potassium permanganate and magnesium sulfate gave methyl (±)-thero-2,3-dihydroxy-4-(3,4-dimethoxyphenyl)-3-methoxycarbonylbutyrate (Va) and its (±)-erythro-isomer (Vb) respectively. The dimethyl esters, (±)-Va and (±)-Vb, were converted to the corresponding monomethyl esters, (±)-VIIa and (±)-VIIb respectively, via two dicarboxylic acid derivatives, (±)-VIa and (±)-VIb. The resolution of (±)-VIIb with brucine gave (+)-VIIb and (−)-VIIb, which were then converted to (+)-Vb and (+)-VIb and to (−)-Vb and (−)-VIb respectively. The synthetic (+)-Vb was shown to be identical with the natural O,O′-dimethylfukiic acid dimethyl ester by a mixed fusion and by comparisons of ...
Details
- ISSN :
- 13480634 and 00092673
- Volume :
- 45
- Database :
- OpenAIRE
- Journal :
- Bulletin of the Chemical Society of Japan
- Accession number :
- edsair.doi...........f51d04162363317458ead61eed24b15a