A short synthesis of (-)-deoxoprosophylline

Syntheses 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)]


Published in:
Heterocycles, 64, 249-259
Year:
2004
Keywords:
Onium compounds Role: RCT (Reactant) ; SPN (Synthetic preparation) ; PREP (Preparation) ; RACT (Reactant or reagent) (iminium ; cyclic; prepn. of (-)-deoxoprosophylline via nucleophilic addn. of Buechi's Grignard reagent to chiral serinal ; intramol. 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 (2S ; 3R ; 6R)-(dodecyl)(hydroxy)-2-piperidinemethanol [(-)-deoxoprosophylline ; Prosopis 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 (2S ; 3R ; 6R)-(dodecyl)(hydroxy)-2-piperidinemethanol [(-)-deoxoprosophylline ; Prosopis alkaloid] using Buechi's Grignard reagent and [bis(phenylmethyl)amino][[(dimethylethyl)dimethylsilyl]oxy]propanal as starting materials); Amination (reductive ; stereoselective; 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 iminium
Note:
CAN 142:374002
31-3
Alkaloids
Institut de Chimie des Substances Naturelles, CNRS,Gif-sur-Yvette,Fr.
Journal
0385-5414
written in English.
100-39-0 (Benzyl bromide) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline intermediate using benzyl bromide as starting material); 349556-02-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline using (+)-(amino)[(phenyl)methoxy](silyl)hexanal as synthetic intermediate); 305838-42-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline using (+)-(hydroxy)[(silyl)methyl]-1,3-dioxolane-2-butanamine as synthetic intermediate); 349555-96-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline using (+)-[(phenyl)methoxy][(silyl)methyl]-1,3-dioxolane-2-butanamine as synthetic intermediate); 849428-93-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline using (-)-(amino)(dodecyl)[(phenyl)methoxy]-1,3-dioxolanepentanol deriv. as synthetic intermediate); 849428-90-6P; 849428-91-7P; 849428-92-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline using (amino)(dodecyl)[(phenyl)methoxy]-1,3-dioxolanepentanol as synthetic intermediate); 349556-03-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline using (amino)[(phenyl)methoxy](silyl)octadecanol deriv. as synthetic intermediate); 143-15-7 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline using (bromo)undecane as starting material); 18742-02-4 (2-(2-Bromoethyl)-1,3-dioxolane); 125654-82-2 ((S)-N,N-Dibenzyl-O-(tert-butyldimethylsilyl)serinal) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline using Buechi's Grignard reagent and [bis(phenylmethyl)amino][[(dimethylethyl)dimethylsilyl]oxy]propanal as starting materials); 849428-94-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline via intramol. reductive amination of (amino)(hydroxy)[(phenyl)methoxy]octadecanone as key synthetic step); 349556-00-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (-)-deoxoprosophylline via stereoselective reductive amination using (+)-(amino)[(phenyl)methoxy](silyl)octadecanone deriv. as synthetic intermediate); 849428-89-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of (2S,3R,6R)-(dodecyl)(hydroxy)-2-piperidinemethanol [(-)-deoxoprosophylline] using Buechi's Grignard reagent and [bis(phenylmethyl)amino][[(dimethylethyl)dimethylsilyl]oxy]propanal as starting materials); 74843-69-9P ((-)-Deoxoprosophylline) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of (2S,3R,6R)-(dodecyl)(hydroxy)-2-piperidinemethanol [(-)-deoxoprosophylline] using Buechi's Grignard reagent and [bis(phenylmethyl)amino][[(dimethylethyl)dimethylsilyl]oxy]propanal as starting materials)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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