The aphid sex pheromone cyclopentanoids: synthesis in the elucidation of structure and biosynthetic pathways was written by Dawson, Glenn W.;Pickett, John a.;Smiley, Diane W. M.. And the article was included in Bioorganic & Medicinal Chemistry in 1996.Synthetic Route of C12H18O3 The following contents are mentioned in the article:
Identification of a range of aphid sex pheromones as comprising the cyclopentanoids (4aS,7S,7aR)-nepetalactone (I), (1R,4aS,7S,7aR)-nepetalactol (II) and the (1S)- and (1R,4aR,7S,7aS)-nepetalactols (III) required samples authenticated by 1H and 13C NMR. These and related compounds were provided by small scale synthesis and extraction from plants in the genus Nepeta (Lamiaceae). The subsequent discovery that the synthetic sex pheromones could attract males, and also parasitic wasps that attack aphids, has created a need for large scale syntheses of the cyclopentanoids. This is afforded by cyclization of the 8-oxo-1-enamine of citronellal as originally developed by Schreiber and co-workers (1986). Investigation into the biosynthesis of the cyclopentanoids by plants for exploiting aphid sex pheromones in crop protection by means of mol. biol. required synthesis of putative biosynthetic intermediates, some with radioactive isotopic labeling, particularly 8-oxidized monoterpene alcs. and aldehydes. This study involved multiple reactions and reactants, such as (2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5Synthetic Route of C12H18O3).
(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate (cas: 37905-02-5) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Synthetic Route of C12H18O3
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics