| Title: | Stereoselective synthesis of dominicalure 1 and 2: Components of aggregation pheromone from male lesser grain borerRhyzopertha dominica (F.) |
| Author(s): | Razkin J; Gil P; Gonzalez A; |
| Address: | "Departamento de Quimica, Universidad Publica de Navarra Campus Arrosadia, 31006, Pamplona, Spain" |
| ISSN/ISBN: | 0098-0331 (Print) 0098-0331 (Linking) |
| Abstract: | "Dominicalure 1 (9a) and dominicalure 2 (9b), were synthesized by esterification of alpha,beta-unsaturated acids4a and4b with (S)-(+)-2-pentanol (8). The key step was the asymmetric reduction of 3-penten-2-one (5) to give the chiral intermediate6, which, upon diimide reduction, DNB derivatization, recrystallization, and hydrolysis, yielded8 in 63% ee. Acids4a and4b were prepared in a simple and efficient three-step synthesis with an overall yield of 54% and 62%, respectively, in stereoisomerically pure form" |
| Notes: | "PubMed-not-MEDLINERazkin, J Gil, P Gonzalez, A eng 1996/04/01 J Chem Ecol. 1996 Apr; 22(4):673-80. doi: 10.1007/BF02033577" |
