[Total synthesis of securinine].
Securinine, an alkaloid having strychnine-like action was synthesized using 1,4-cyclohexanedione as the starting material through the following sequence of reactions: condensation with piperidine, reduction, cyclization catalyzed by mercuric acetate and intramolecular condensation, totally in eleven steps. The IR, 1HNMR and melting point of the synthetic product is identical with those of natural securinine.
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Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing.
Liang
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D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones; D010880:Piperidines
D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones; D010880:Piperidines; C000785:securinine