Stereoselective synthesis of dominicalure 1 and 2: Components of aggregation pheromone from male lesser grain borer Rhyzopertha dominica (F.)

Article abstract of DOI:10.1007/BF02033577

Dominicalure 1 (9a) and dominicalure 2 (9b), were synthesized by esterification of α,β-unsaturated acids 4a and 4b with (5)-(+)-2-pentanol (8). The key step was the asymmetric reduction of 3-penten-2-one (5) to give the chiral intermediate 6, which, upon diimide reduction, DNB derivatization, recrystallization, and hydrolysis, yielded 8 in 63% ee. Acids 4a and 4b were prepared in a simple and efficient three-step synthesis with an overall yield of 54% and 62%, respectively, in stereoisomerically pure form.