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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
Author(s) -
Ballini Roberto,
Astolfi Paola
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619961124
Subject(s) - chemistry , ene reaction , yield (engineering) , nitro , alcohol , component (thermodynamics) , nitrous acid , catalysis , organic chemistry , alkyl , materials science , physics , metallurgy , thermodynamics
( 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.