A short and efficient enantioselective synthesis of (+) and (-)-(Z)-7,15-hexadecadien-4-olide: the sex pheromone of the yellowish elongate chafer, Heptophylla picea

Clososki, Giuliano C.; Ricci, Luís C.; Costa, Carlos Eduardo da; Comasseto, J. V.

doi:10.1590/s0103-50532004000600004

Cited by 2 publications

(2 citation statements)

References 7 publications

(15 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…10-Homonerol (98%) and 10-homonerol oxide (97%) were synthesized as described by Baeckstrom et al (1982) and Cahiez et al (1976), respectively. (Z)-6-Tridecen-2-ol (90%) and (Z)-6-undecen-2-ol (90%) were synthesized according to Clososki et al (2004). The Benallure™ dispensers were purchased from Gardens Alive, Inc., Lawrenceburg, IN, USA.…”

Section: Insects and Chemicalsmentioning

confidence: 99%

Serendipitous, cross familial discovery of the first long-range chemical attractants for antlions (Neuroptera: Myrmeleontidae): (1R,2S,5R,8R)-iridodial and Z,E-nepetalactol

et al. 2015

View full text Add to dashboard Cite

Synthetic (1R,2S,5R,8R)-iridodial, the key pheromone component of many green lacewings in the genus Chrysopa, strongly attracted adult males and females of the North American antlion, Dendroleon speciosus Banks. In addition, one of the common sex pheromone components of many aphids to which Chrysopa spp. are weakly attracted, Z,E-nepetalactol, was also weakly attractive to D. speciosus adults. Iridodial and Z,E-nepetalactol also elicited strong and weak electroantennogram detector (EAD) responses, respectively, in D. speciosus adults. Previously reported semiochemicals from European and Israeli antlion species did not elicit EAD or behavioral responses from D. speciosus adults. The earlier studied antlions release volatile chemicals from male-specific metathoracic glands associated with structures on the hind wings (Eltringham's organs) that are thought to enhance evaporation of the secretion. Although D. speciosus males have Eltringham's organs similar to those of other antlion species, we discovered that D. speciosus males have a pair of white tubular glands that extend posteriorly into the abdomen, opening in the resting pits of the Eltringham's organs. Further gas chromatograph (GC)-EAD analysis of another commercially available antlion species, Myrmeleon crudelis Walker, showed that this species did not respond to the lacewing or aphid related volatile compounds, but strongly responded to the reported antlion semiochemicals, namely, nerol, 10-homonerol, and nerol oxide. The male-specific abdominal glands of D. speciosus are presumably pheromone glands, but this hypothesis requires verification in the future.

show abstract

Section: Insects and Chemicalsmentioning

confidence: 99%

Serendipitous, cross familial discovery of the first long-range chemical attractants for antlions (Neuroptera: Myrmeleontidae): (1R,2S,5R,8R)-iridodial and Z,E-nepetalactol

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Clososki et al 127 described an enzymatic synthesis of (R)-and (S)-38. A known lipase-catalysed enantiolactonization in the key step afforded a common precursor for both enantiomers of the pheromone, in 92% e.e.…”

Section: (Z)-715-hexadecadien-4-olide (38)mentioning

confidence: 99%

Insect pheromone synthesis in Brazil: an overview

Zarbin¹,

Villar²,

Corrêa³

2007

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Nesta revisão estão descritas as sínteses de feromônios de insetos desenvolvidas e publicadas por grupos de pesquisa brasileiros, e tem por objetivo apresentar o estado da arte desta área de pesquisa no país e fornecer uma informação rápida sobre as moléculas já sintetizadas e metodologias empregadas. As sínteses estão apresentadas em ordem cronológica, exceto quando se trata de diferentes metodologias para a mesma molécula.This review describes the syntheses of insect pheromones developed and published by Brazilian research groups and aims to present the state of the art of this area in the country, and also to serves as a quick view of the already synthesized molecules and employed methodology. The syntheses are presented in chronological order, except when they refer to different approaches for the same molecule.

show abstract

A short and efficient enantioselective synthesis of (+) and (-)-(Z)-7,15-hexadecadien-4-olide: the sex pheromone of the yellowish elongate chafer, Heptophylla picea

Cited by 2 publications

References 7 publications

Serendipitous, cross familial discovery of the first long-range chemical attractants for antlions (Neuroptera: Myrmeleontidae): (1R,2S,5R,8R)-iridodial and Z,E-nepetalactol

Serendipitous, cross familial discovery of the first long-range chemical attractants for antlions (Neuroptera: Myrmeleontidae): (1R,2S,5R,8R)-iridodial and Z,E-nepetalactol

Insect pheromone synthesis in Brazil: an overview

Contact Info

Product

Resources

About