A Convenient Synthesis of (E)-Non-3-ene-2,5-dione, an Important Component Isolated from the Fire BeeTrigona tataira

✍ Scribed by Ballini, Roberto ;Astolfi, Paola

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 190 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619961124

✦ Synopsis

Abstract

(E)‐Non‐3‐ene‐2,5‐dione (5) the main component isolated from the volatile compounds derived from the cephalic secretion of workers of Trigona tataira, was conveniently prepared by nitroaldol reaction between pentanal 1 and 1‐nitrobutan‐3‐ol (rac‐2) catalyzed by Amberlyst A‐21. The resulting β‐nitro alcohol rac‐3 was oxidized to the α‐nitro ketones 4, which via elimination of nitrous acid (Et~3~N), afforded the enedione 5 in good yield.