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 configura...

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Veröffentlicht in:	Carbohydrate research 2006-11, Vol.341 (16), p.2653-2657
Hauptverfasser:	Liu, Jun, Du, Yuguo, Dong, Xiaomin, Meng, Shucong, Xiao, Junjun, Cheng, Lijian
Format:	Artikel
Sprache:	eng
Schlagworte:	Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Antitumor activity Carbohydrates Cell Line, Tumor - drug effects HeLa Cells Humans Jaspine B Natural products Sphingosine - analogs & derivatives Sphingosine - chemical synthesis Sphingosine - pharmacology Stereoisomerism Total synthesis Xylose - chemistry
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Beschreibung
Zusammenfassung:	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.
ISSN:	0008-6215 1873-426X
DOI:	10.1016/j.carres.2006.08.011