The total synthesis of (±) kawain via a hetero-diels-alder cycloaddition

✍ Scribed by Stephen Castellino; James J. Sims

• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 199 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)90181-9

✦ Synopsis

The hetero-Diels-Alder reaction between 1,3-dimethoxy-1-trimethylsilyloxybutadlene 4, and cinnamaldehyde 5, produces (+) kawain in 75% and 84% yield respectively when catalyzed by Eu(fod)g or Yb(fod)g. When Ag(fod) is employed as the catalyst a unique condensation reaction occurs which produces two acyclic diastereomers in 72% yield.