6 2-Acylindole Alkaloidsの合成研究 : Vobasine骨格の合成
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We have carried out the first synthesis of 1-methy1-16-decarbomethoxy-20-desethylidenevobasine (IV) having the carbon skeleton of the 2-acylindole alkaloids which are represented by vobasine (I). Dimethyl esters (VIIIa, b), which were respectively obtained from N-benzyltryptophan methyl ester (VIIa) and its 1-methyl derivative (VIIb), were subjected to the Dieckmann cyclization reaction to furnish the methyl β-ketoesters (IXa, b). Alcoholysis of IXa, b with benzyl alcohol followed by alkylation with benzyl bromoacetate gave the dibenzyl esters (XIa, b), which were catalytically hydrogenated and decarboxylated to afford the carboxylic acids (XIIa, b). The Huang-Minlon reduction of XIIa, b to XIIIa, b was followed by cyclization with polyphosphoric acid to give the tetracyclic keto lactams (XIVa, b), which were reduced by lithium aluminum hydride to the alcohols (XVa, b), and the latter were oxidized with chromic acid in pyridine to the ketones (XVIa, b). XVIa, b resisted the catalytic debenzylation over palladium-carbon, and only XVIb yielded a small amount of the carbinolamine (XVIIb). Thus XIIIb-1 was debenzylated with sodium in liquid ammonia, and the product (XVIIIb) was successively treated as above with polyphosphoric acid, lithium aluminum hydride and chromic acid to give XVIIb. Finally, methylation of XVIIb with formic acidformalin afforded the desired vobasine derivative (IV).
- 天然有機化合物討論会の論文
- 1966-09-15
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