Publication
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)]
Majed Chergui, Oliviero Cannelli, Giulia Fulvia Mancini, Malte Oppermann, Camila Bacellar Cases Da Silveira, Dominik Kinschel, Christian David, Jérôme Lacour
Hatice Altug, Felix Ulrich Richter, Yasaman Jahani, Rui Lu, Bang Hyun Lee, Ming-Lun Tseng, Longfang Ye
Oleg Yazyev, Jan Hugo Dil, Quansheng Wu, Shengnan Zhang