Chiron approach to the synthesis of (2S,3R)-3-hydroxypipecolic acid and (2R,3R)-3-hydroxy-2-hydroxymethylpiperidine from D-glucose

The first chiron approach from d-glucose for the total synthesis of (2 S,3 R)-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.