• Media type: E-Article
  • Title: Asymmetric Synthesis and in vivo Biological Inactivity of the Right‐Hand Terpenoid Fragment of Terpendole E
  • Contributor: Oikawa, Masato; Hashimoto, Ryo; Sasaki, Makoto
  • Published: Wiley, 2011
  • Published in: European Journal of Organic Chemistry, 2011 (2011) 3, Seite 538-546
  • Language: English
  • DOI: 10.1002/ejoc.201001104
  • ISSN: 1434-193X; 1099-0690
  • Keywords: Organic Chemistry ; Physical and Theoretical Chemistry
  • Origination:
  • Footnote:
  • Description: <jats:title>Abstract</jats:title><jats:p>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.</jats:p>