Synthesis of (±)-sesbanine via directed metalation of tertiary nicotinamides

✍ Scribed by Masatomo Iwao; Tsukasa Kuraishi

• Book ID: 104221339
• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 210 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87968-x

✦ Synopsis

Racemic sesbanine was synthesized by using regioselective ortho lithiation of N,N-dialkylnicotinamides and subsequent condensation with 3cyclopentenone as key reactions. Diverse synthetic utility of tertiary amide-directed metalation of aromatic substrates has been demonstrated by Snieckus and co-workers in the syntheses of highly substituted aromatics, polycyclic aromatic hydrocarbons,