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Synthesis of degraded cyanogenic glycosides from Sambucus nigra
Marina Dellagreca1, Antonio Fiorentino, Pietro Monaco
1Dipartimento di Chimica Organica e Biochimica, Università Federico II, Complesso Universitario Monte S. Angelo, Via Cinthia, 1-80134 Napoli, Italy.
Natural Product Research
|May 10, 2003
Abstract:
Two natural cyanohydrins, isolated from Sambucus nigra, have been synthesised from mandelonitrile and penta-O-acetyl-beta-galactopyranose. The synthesis confirmed the stereochemistry of the compounds, which had been assigned on biogenetic grounds.
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01:32Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
01:10Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...