Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Stereoselective Synthesis of L-Deoxyaltronojirimycin from L-Serine

  • Rengasamy, Rajesh (Division of Applied Life Science (BK21 program), EB-NCRC, Institute of Agriculture & Life Science,Gyeongsang National University) ;
  • Curtis-Long, Marcus J. (12 New Road, Nafferton, Driffield) ;
  • Ryu, Hyung-Won (Division of Applied Life Science (BK21 program), EB-NCRC, Institute of Agriculture & Life Science,Gyeongsang National University) ;
  • Oh, Kyeong-Yeol (Division of Applied Life Science (BK21 program), EB-NCRC, Institute of Agriculture & Life Science,Gyeongsang National University) ;
  • Park, Ki-Hun (Division of Applied Life Science (BK21 program), EB-NCRC, Institute of Agriculture & Life Science,Gyeongsang National University)
  • Published : 2009.07.20
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Abstract

(2S,3R)-3-Hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine 8, an important precursor for the synthesis of polyhydroxylated piperidine azasugars, has been prepared from L-serine. Highly stereoselective nucleophilic addition to amino aldehyde 5 gave the corresponding allylic alcohol 6 which proceeded to give dihydro-2H-piridine 7a via a Grubbs II catalyzed RCM. Stereoselective H-bond directed epoxidation of allylic alcohol led to the oxiranyl alcohol 9 which was easily converted to L-deoxyaltronojirimycin by regioselective ring opening.

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References

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