Abstract
This paper describes the synthesis of pheromones and jasmonoids from acrylaldehyde diethyl acetal (1). The synthetic route is shown in Scheme-1.
The radical addition reaction of aldehyde with (1) was carried out with benzoyl peroxide as the initiator in N2 atomosphere. γ-Oxoaldehyde acetal [(6), (7), (8), (9)] was obtained as the major product by this reaction.
cis-12-Nonadecen-9-one (14) was synthesized from 1, 1-diethoxy-4-oxododecanal (11) prepared from (7), by Wittig reaction in 62% yield. Similarly, cis-13-icosen-1O-one (15) and cis-5-undecen-2-one (16) were prepared from γ-oxoaldehyde in 6062% yield.
Methyl jasmonate (18) and cis-jasmone (19) were synthesized from 2- (cis-2-pentenyl) -2-cyclopentenone (17) prepared from 4-oxo-cis-7-decenal (10), according to the published method. γ-Jasmolactone (21) was prepared from 1, 1-diethoxy-cis-7-decen-4-ol (20) by Jones oxidation in 88% yield.
