Synthesis of D-erythro-sphingosine and D-erythro-ceramide.
A 1,2-metallate rearrangment of a higher order cuprate derived from an alpha-lithiated xylal derivative and tridecyllithium is the key step in a synthesis of D-erythro-sphingosine and ceramide. A convenient method for preparing alpha-lithiated glycals from alpha-phenylsulfinyl glycals is also described.
Milne
Jacqueline E
JE
Department of Chemistry, Leeds University, Leeds, UK LS2 9JT.
Jarowicki
Krzysztof
K
Kocienski
Philip J
PJ
Alonso
Jorge
J
D002518:Ceramides / Q000138:chemical synthesis*; D003300:Copper / Q000737:chemistry; D013110:Sphingosine / Q000138:chemical synthesis*; D014994:Xylose / Q000737:chemistry
D002518:Ceramides; C042514:cuprous ion; D003300:Copper; D014994:Xylose; D013110:Sphingosine