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