Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 3, Pages 538-546Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001104
Keywords
Natural products; Terpenoids; Radical reactions; Reduction; Metathesis; Cyclization; Inhibitors
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Synthesis of the DEF-ring terpenoid fragment of terpendole E, an Eg5 inhibitor, is described. The DE-ring was constructed by a modification of Barrero's radical cyclization. The F-ring tetrahydropyran was then constructed by acid-induced cyclization of an epoxy alcohol, which was prepared by cross-metathesis followed by Shi's epoxidation. Cell-based assays indicated that the DEF-ring fragment is not capable of inhibiting cell growth and cell cycle progression of human cancer cell lines, indicating that the DEF-ring fragment alone is not sufficient for the biological activity.
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