ISSN:
1573-1561
Keywords:
Pheromone
;
Rhyzopertha dominica
;
Coleoptera
;
Bostrichidae
;
dominicalure
;
(S)-(+)-2-pentanol
;
asymmetric reduction
;
(E)-2-methyl-2-pentenoic acid
;
(E)-2,4-dimethyl-2-pentenoic acid
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
,
Chemistry and Pharmacology
Notes:
Abstract Dominicalure 1 (9a) and dominicalure 2 (9b), were synthesized by esterification of α,β-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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF02033577
Permalink
