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

1996; Wiley; Volume: 1996; Issue: 11 Linguagem: Inglês

10.1002/jlac.199619961124

0947-3440

Roberto Ballini, Paola Astolfi,

Traditional and Medicinal Uses of Annonaceae

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.