Regioselective ring-closing metathesis on terpenoid acrylates and acrylamides

✍ Scribed by Yanming Du; David F Wiemer

• Book ID: 104231236
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 104 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01179-0

✦ Synopsis

A series of acrylate esters was prepared by treatment of representative terpenoid aldehydes with allyl or vinyl magnesium bromide followed by reaction with acryloyl chloride. In all cases, ring-closing metathesis (RCM) resulted in regioselective formation of unsaturated lactones through metathesis of the acrylate and terminal olefins. After condensation of farnesal with a primary amine, a parallel series of reactions led to formation of the corresponding lactam.