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.
Kalamkar
Navnath B
NB
Department of Chemistry, Garware Research Centre, University of Pune, Pune - 411 007, India.
Kasture
Vijay M
VM
Dhavale
Dilip D
DD
D002384:Catalysis; D005947:Glucose / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D008670:Metals / Q000737:chemistry; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D014765:Viral Vaccines / Q000737:chemistry*
C529506:3-hydroxy-2-hydroxymethylpiperidine; C529304:3-hydroxypipecolic acid; D008670:Metals; D010875:Pipecolic Acids; D010880:Piperidines; D014765:Viral Vaccines; C409203:chiron; D006859:Hydrogen; D005947:Glucose