Stereoselective synthesis of jaspine B from D-xylose.
The natural cytotoxic marine compound, jaspine B, is stereoselectively synthesized from D-xylose in 11 linear steps with a 23.9% overall yield. The key step in the synthesis involves an iodine-induced debenzylation of a primary alcohol and the subsequent 2,5-cyclization to fit the required configuration of jaspine B. A preliminary bioassay shows strong inhibition activities against human MDA231, Hela, and CNE cell lines, indicating potential usage in various cancer treatments.
Liu
Jun
J
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
Du
Yuguo
Y
Dong
Xiaomin
X
Meng
Shucong
S
Xiao
Junjun
J
Cheng
Lijian
L
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013237:Stereoisomerism; D014994:Xylose / Q000737:chemistry*
D000970:Antineoplastic Agents; C468594:pachastrissamine; D014994:Xylose; D013110:Sphingosine