Jourdant, AngeliqueZhu, Jieping2010-11-252010-11-252010-11-25200410.3987/COM-04-S(P)21https://infoscience.epfl.ch/handle/20.500.14299/58478Syntheses of (-)-deoxoprosophylline from chiral L-N,N-di(benzyl)serine (TBDMS) aldehyde is reported. A highly diastereoselective nucleophilic addn. of Buechi's Grignard reagent to chiral serinal followed by an intramol. reductive amination of w-oxo amino diol are two key steps of the present synthesis. The target compd. was (2S,3R,6R)-6-dodecyl-3-hydroxy-2-piperidinemethanol, which is related to the Prosopis africana piperidine alkaloid family. [on SciFinder (R)]Onium compounds Role: RCT (Reactant)SPN (Synthetic preparation)PREP (Preparation)RACT (Reactant or reagent) (iminiumcyclic; prepn. of (-)-deoxoprosophylline via nucleophilic addn. of Buechi's Grignard reagent to chiral serinalintramol. reductive amination of w-oxo amino diol and formation of cyclic iminium intermediate as key synthetic steps); Alkaloids Role: SPN (Synthetic preparation)PREP (Preparation) (piperidine; prepn. of (2S3R6R)-(dodecyl)(hydroxy)-2-piperidinemethanol [(-)-deoxoprosophyllineProsopis alkaloid] using Buechi's Grignard reagent and [bis(phenylmethyl)amino][[(dimethylethyl)dimethylsilyl]oxy]propanal as starting materials); Asymmetric synthesis and induction (prepn. of (-)-deoxoprosophylline via diastereoselective nucleophilic addn. of Buechi's Grignard reagent to chiral serinal and intramol. reductive amination of w-oxo amino diol intermediate as key synthetic steps); Prosopis africana (prepn. of (2S3R6R)-(dodecyl)(hydroxy)-2-piperidinemethanol [(-)-deoxoprosophyllineProsopis alkaloid] using Buechi's Grignard reagent and [bis(phenylmethyl)amino][[(dimethylethyl)dimethylsilyl]oxy]propanal as starting materials); Amination (reductivestereoselective; prepn. of (-)-deoxoprosophylline via reductive amination using (+)-(amino)[(phenyl)methoxy](silyl)octadecanone deriv. as synthetic intermediate)deoxoprosophylline piperidinemethanol dodecyl hydroxy asym synthesis; reductive amination stereoselective amino hydroxy silyl octadecanone prepn deoxoprosophylline; Prosopis africana piperidine alkaloid deoxoprosophylline stereoselective reductive amination iminiumtext::journal::journal article::research article