Tetrahedron

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

C Xarnod, W Huang, RG Ren, RC Liu, BG Wei

Index: Chao, Cholmen Xarnod Lu-Men; Huang, Wei; Ren, Rong-Guo; Liu, Ru-Cheng; Wei, Bang-Guo Tetrahedron, 2012 , vol. 68, # 33 p. 6688 - 6695

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Citation Number: 19

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 SmI2- 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 ...

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