Kinetically Controlled Ring-Closing Metathesis: Synthesis of a Potential Scaffold for 12-Membered Salicylic Macrolides

✍ Scribed by Yuji Matsuya; Sho-ichi Takayanagi; Hideo Nemoto

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 281 KB
• Volume: 14
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200800249

✦ Synopsis

Abstract

For the synthesis of a 12‐membered salicylic macrolide scaffold, ring‐closing metathesis (RCM) of a ω‐diene compound was planned. The stereochemical outcome of the RCM reaction changed depending on the type of Ru catalyst that was used; a “first‐generation” Grubbs catalyst produced exclusively the E isomer and “second‐generation” catalysts provided a mixture of the E and Z isomers under kinetic control (not thermodynamic control). Considerations for the E/Z selectivity are described.