A Convenient Synthesis of (E)-Non-3-ene-2,5-dione, an Important Component Isolated from the Fire Bee Trigona tataira
Nitrous acid elimination
Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
(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 (Et3N), afforded the enedione 5 in good yield.
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