Short Synthesis of Vesperal [(S)-10-Oxoisopiperitenone], the Female Sex Pheromone of the Longhorn Beetle (Vesperus xatarti), and of Its Enantiomer

✍ Scribed by Kenji Domon; Kenji Mori

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 223 KB
• Volume: 2000
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200011)2000:22<3783::aid-ejoc3783>3.0.co;2-o

✦ Synopsis

steps). The non-natural (R)-vesperal was also prepared from (S)-limonene. Scheme 2. Synthesis of vesperal (1): reagents: (a) (i) nBuLi, TMEDA; (ii) O 2 (iii) 25% Na 2 SO 3 aq. soln. (30%); (b) Ac 2 O, C 5 H 5 N (quant.); (c) MCPBA, NaHCO 3 , CH 2 Cl 2 (86%); (d) Ph 2 Se 2 , NaBH 4 , EtOH (70% of 7 and 17% of 8); (e) 34% H 2 O 2 , THF/H 2 O (65%); (f) PCC, NaOAc, CH 2 Cl 2 , (54%).

Another advantage of employing limonene (3) as the starting material is the fact that both (R)-and (S)-3 are