Asymmetric Synthesis and in vivo Biological Inactivity of the Right-Hand Terpenoid Fragment of Terpendole E

✍ Scribed by Masato Oikawa; Ryo Hashimoto; Makoto Sasaki

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 627 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201001104

✦ Synopsis

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.