The Synthesis and Configuration of Fukiic Acid Derivatives

Autor:	Teruko Nakayama, Takashi Matsumoto, Kazuo Hidaka, Kenji Fukui
Rok vydání:	1972
Předmět:	chemistry.chemical_classification animal structures Brucine Aqueous solution Magnesium chemistry.chemical_element General Chemistry Medicinal chemistry Dimethyl ester chemistry.chemical_compound Potassium permanganate Dicarboxylic acid chemistry Wittig reaction Organic chemistry Fukiic acid
Zdroj:	Bulletin of the Chemical Society of Japan. 45:1501-1504
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.45.1501
Popis:	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 ...
Databáze:	OpenAIRE
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