A flexible approach to construct three contiguous chiral centers of sphingolipids, and asymmetric synthesis of d-ribo-phytosphingosine and its derivatives

@article{Xarnod2012AFA,
  title={A flexible approach to construct three contiguous chiral centers of sphingolipids, and asymmetric synthesis of d-ribo-phytosphingosine and its derivatives},
  author={Cholmen Xarnod and W. Huang and Rong‐Guo Ren and Ru-Cheng Liu and Bang-Guo Wei},
  journal={Tetrahedron},
  year={2012},
  volume={68},
  pages={6688-6695}
}
Abstract An efficient approach to build the three contiguous stereogenic centers of sphingosine unit starting from cheap glutamic acid is described. The key step of this approach is the SmI 2 -mediated cross-coupling of chiral N - tert -butanesulfinyl imine 11 with sterically hindered aliphatic aldehyde 9 or 21 to construct hydroxymethyl β-amino alcohol 10 or 22 in high diastereoselectivity (>99%, de). The utility of this flexible method has been demonstrated in the synthesis of d - ribo… Expand
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