A 1,2-metallate rearrangment of a higher order cuprate derived from an α-lithiated xylal derivative and tridecyllithium is the key step in a synthesis of D-erythro-sphingosine and ceramide. A convenient method for preparing α-lithiated glycals from α-phenylsulfinyl glycals is also described.
J. E. Milne, K. Jarowicki, P. J. Kocienski and J. Alonso, Chem. Commun., 2002, 426 DOI: 10.1039/B111071N
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