Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) from D-xylose.
The first naturally occurring anhydrophytosphingosine, pachastrissamine (jaspine B), a marine compound cytotoxic toward P388, A549, HT29, and MEL28 cell lines at IC(50) = 0.01 microg/mL level, has been stereoselectively synthesized from D-xylose in 10 linear steps with 25.7% overall yield.
Du
Yuguo
Y
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China. duyuguo@mail.rcees.ac.cn
Liu
Jun
J
Linhardt
Robert J
RJ
D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D013237:Stereoisomerism; D014994:Xylose / Q000737:chemistry*
C468594:pachastrissamine; D014994:Xylose; D013110:Sphingosine