Asymmetric synthesis and in vivo biological inactivity of the right-hand terpenoid fragment of terpendole e

Masato Oikawa, Ryo Hashimoto, Makoto Sasaki

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

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. The DEF-ring terpenoid fragment of terpendole E, has been synthesized in 15 steps starting from farnesyl acetate, employing radical cyclization (DE-ring formation) and stereoselective cyclization of an epoxyalcohol (F-ring formation). Cell-based assays showed that the right-hand DEF-ring fragment is inactive in cell growth and cell cycle progression of human cancer cell lines.

Original languageEnglish
Pages (from-to)538-546
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number3
DOIs
Publication statusPublished - 2011 Jan

Keywords

  • Cyclization
  • Inhibitors
  • Metathesis
  • Natural products
  • Radical reactions
  • Reduction
  • Terpenoids

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