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Diastereoselective Synthesis of 1,6-Diepicastanospermine from D-Glucono-δ-lactone

  • Jang, Ki-Chang (Division of Applied Life Science (BK21 program), Department of Agricultural Chemistry, Gyeongsang National University) ;
  • Choi, Sung-Jun (Division of Applied Life Science (BK21 program), Department of Agricultural Chemistry, Gyeongsang National University) ;
  • Kim, Jin-Hyo (Division of Applied Life Science (BK21 program), Department of Agricultural Chemistry, Gyeongsang National University) ;
  • Lee, Jin-Hwan (Division of Applied Life Science (BK21 program), Department of Agricultural Chemistry, Gyeongsang National University) ;
  • Lee, Byong-Won (Division of Applied Life Science (BK21 program), Department of Agricultural Chemistry, Gyeongsang National University) ;
  • Park, Ki-Hun (Division of Applied Life Science (BK21 program), Department of Agricultural Chemistry, Gyeongsang National University)
  • Published : 2003.07.20
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Abstract

Homochiral (-)-pipecolaldehyde 6 from D-glucono- δ-lactone underwent a highly diastereoselective addition upon treatment with vinylmagnesium bromide. Treatment with vinylmagnesium bromide produced antiaminoalcohol 7a which was easily converted into the synthesis of 1,6-diepicastanospermine 2.

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References

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  1. Diastereoselective Synthesis of 1,6-Diepicastanospermine from D-Glucono-δ-lactone. vol.35, pp.1, 2003, https://doi.org/10.1002/chin.200401183
  2. Indolizidine and quinolizidine alkaloids vol.22, pp.5, 2005, https://doi.org/10.1039/b413748p