1021428-01-2Relevant academic research and scientific papers
Chiron approach to the synthesis of (2S,3R)-3-hydroxypipecolic acid and (2R,3R)-3-hydroxy-2-hydroxymethylpiperidine from D-glucose
Kalamkar, Navnath B.,Kasture, Vijay M.,Dhavale, Dilip D.
, p. 3619 - 3622 (2008/09/20)
(Chemical Equation Presented) The first chiron approach from D-glucose for the total synthesis of (2S,3R)-3-hydroxypipecolic acid (-)-1a and (2R,3R)-3-hydroxy-2-hydroxymethylpiperidine (-)-2a is reported. The synthetic pathway involves conversion of D-glucose into 3-azidopentodialdose (5) followed by the Wittig olefination and reduction to give the piperidine ring skeleton (8) with a sugar appendage that on cleavage of an anomeric carbon followed by oxidation gives (-)-1a which on reduction affords (-)-2a.
