152212-36-7Relevant articles and documents
The male pheromone of the old house borer Hylotrupes banjulus (L.) (Coleoptera: Cerambycidae): Identification and female response
Fettkother,Dettner,Schroder,Meyer,Francke,Noldt
, p. 270 - 277 (1995)
We report here the identification of the long-range, male-produced sex pheromone of the Old house borer Hylotrupes bajulus. Chemical analysis of hexane extracts obtained by surface extraction from dissected prothoracic glands and from headspace samples of the two sexes, revealed male-specific compounds: (3R)-3-hydroxy-2-hexanone, 2-hydroxy-3-hexanone, the diastereomeric diols (2R, 3R)-2,3-hexanediol and (2S, 3R)-2,3-hexanediol, 2,3-hexanedione, as well as 1-butanol. In wind tunnel bioassays we tested the influence of these male-specific compounds from the prothoracal glands on the behaviour of unmated and mated females. Specific behavioural sequences of the tested females (activity, running behaviour, searching, cleaning, flying, extension of ovipositor) were recorded. Unmated females were attracted by male beetles, headspace extracts of males, synthetic blends of the major pheromone compounds as well as by the components (3R)-3-hydroxy-2-hexanone, and the diastereomeric diols. Hexane, female beetles and 2,3-hexanedione did not attract unmated females. The reactions of mated females to male beetles and headspace samples did not differ significantly from those of the controls. The results of the bioassays show that the two-stage premating behaviour is initiated by emission of a long-range sex pheromone from the male prothoracal glands, which functions as an activator, attractant, and possibly aphrodisiac for unmated females.
Synthesis of Longhorn Beetle Pheromone Components by Proline-Mediated α-Hydroxylation of Alkyl Ketones
Do Carmo, Hugo,Amorós, María Eugenia,González, Andrés,Heguaburu, Viviana Lucía
, p. 4501 - 4506 (2021/08/17)
The stereoselective synthesis of several components of the aggregation pheromones of numerous longhorn beetle species is described. These attractants consist of 3-hydroxy-2-alkanones and 2,3-alkyldiols with chain lengths varying from six to ten carbons. T
Enzymatic Cross-Benzoin-Type Condensation of Aliphatic Aldehydes: Enantioselective Synthesis of 1-Alkyl-1-hydroxypropan-2-ones and 1-Alkyl-1-hydroxybutan-2-ones
Di Carmine, Graziano,Bortolini, Olga,Massi, Alessandro,Müller, Michael,Bernacchia, Giovanni,Fantin, Giancarlo,Ragno, Daniele,Giovannini, Pier Paolo
supporting information, p. 4132 - 4141 (2018/09/12)
Benzoin-type reactions have been intensively exploited as a synthetic strategy for the preparation of α-hydroxy ketones. Thiamine diphosphate (ThDP) dependent enzymes are excellent catalysts for asymmetric versions of such reaction types. In particular, in cross-benzoin condensations of aromatic reactants and mixed aromatic/aliphatic reactions, use of these enzymes has resulted in high levels of chemo-, regio- and stereoselectivity. The present work, which confirms this trend for aliphatic reactants, outlines results obtained in the formal cross-benzoin-type condensation of the ‘umpoled’ acetaldehyde and propionaldehyde with various aliphatic aldehydes catalyzed by the ThDP-dependent enzyme acetoin:dichlorophenolindophenol oxidoreductase (Ao:DCPIP OR). In these reactions, 3-hydroxy-3-methylbutan-2-one (methylacetoin) was used as the activated acetaldehyde donor, while 4-hydroxy-4-methylhexan-3-one was employed for the first time as the precursor of activated propionaldehyde. With the exception of 3-hydroxypentan-2-one and 3-hydroxyhexan-2-one, which were obtained in almost racemic form by the condensation of methylacetoin with propanal and butanal, respectively, all other products achieved from reactions performed using the same donor with more hindered aldehyde acceptors were obtained with high conversions (89–99%) and in good to high enantiomeric excess (72–99% ee). In a similar way, high conversions (75–99%) and good ee (76–99%) were observed in reactions performed with the same set of aldehyde acceptors, but using 4-hydroxy-4-methylhexan-3-one as propionyl anion donor. This is the first time that most of the products described herein have been prepared via benzoin-type condensation. (Figure presented.).
