Synthesis of longhorn beetle pheromone components by proline mediated α-hydroxylation of alkylketones

Enantiomeric Excess ◽

Aggregation Pheromones ◽

Beetle Species ◽

Enantiomerically Pure ◽

Longhorn Beetle ◽

Pheromone Components ◽

Chain Lengths

The stereoselective synthesis of several components of the aggregation pheromones of numerous longhorn beetle species is described. These attractants consist in 3-hydroxy-2-alkylketones and 2,3-alkyldiols with chain lengths varying from six to ten carbons. The 3R- and 3S-series are generated by organocatalytic α-hydroxylation of alkylketones with nitrosobenzene in the presence of L- or D-proline, respectively, to obtain the hydroxyketones in high enantiomeric excess. Further reduction and chromatographic separation leads to the enantiomerically pure diols that complete the library

Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis

Angewandte Chemie International Edition ◽

10.1002/anie.201506906 ◽

2015 ◽

Vol 54 (46) ◽

pp. 13764-13768 ◽

Cited By ~ 20

Author(s):

Wilko Greschner ◽

Beate Neumann ◽

Hans-Georg Stammler ◽

Harald Gröger ◽

Dietmar Kuck

Keyword(s):

Direct Stereoselective Synthesis of Enantiomerically Pure anti-β-Amino Alcohols

The Journal of Organic Chemistry ◽

10.1021/jo500481j ◽

2014 ◽

Vol 79 (15) ◽

pp. 6775-6782 ◽

Cited By ~ 22

Author(s):

Gastón Silveira-Dorta ◽

Osvaldo J. Donadel ◽

Víctor S. Martín ◽

José M. Padrón

Keyword(s):

Amino Alcohols ◽

Stereoselective Synthesis of Enantiomerically Pure Piperidine Derivatives by N-Galactosylation of Pyridones.

ChemInform ◽

10.1002/chin.200446139 ◽

2004 ◽

Vol 35 (46) ◽

Author(s):

Ellen Klegraf ◽

Markus Follmann ◽

Dieter Schollmeyer ◽

Horst Kunz

Keyword(s):

Synthesis of enantiomerically pure alcohols and amines via biocatalytic deracemisation methods

Catalysis Science & Technology ◽

10.1039/c9cy01539f ◽

2019 ◽

Vol 9 (20) ◽

pp. 5487-5503 ◽

Cited By ~ 14

Author(s):

Musa M. Musa ◽

Frank Hollmann ◽

Francesco G. Mutti

Keyword(s):

Kinetic Resolution ◽

Enantiomeric Excess ◽

Enantiomerically Pure ◽

Theoretical Maximum

Deracemisation via chemo-enzymatic or multi-enzymatic approaches is the optimum substitute for kinetic resolution, which suffers from the limitation of a theoretical maximum 50% yield albeit high enantiomeric excess is attainable.

Exploiting trap color to improve surveys of longhorn beetles

Journal of Pest Science ◽

10.1007/s10340-020-01303-w ◽

2020 ◽

Author(s):

Giacomo Cavaletto ◽

Massimo Faccoli ◽

Lorenzo Marini ◽

Johannes Spaethe ◽

Filippo Giannone ◽

...

Keyword(s):

Block Design ◽

Beetle Species ◽

Mixed Response ◽

Longhorn Beetles ◽

Longhorn Beetle ◽

Trap Color ◽

Surveillance Programs ◽

Materials Used ◽

Flower Visiting ◽

Species Richness And Abundance

AbstractLonghorn beetles are commonly moved among continents within wood packaging materials used in trades. Visual inspections carried out at points of entry often fail to detect exotic longhorn beetles as infested materials may have little or no sign of colonization. Black-colored traps baited with pheromones and host volatiles are thus used to improve chances of detection. Here we tested whether existing surveillance protocols for longhorn beetles can be further improved using trap colors different than black. Baited traps of eight different colors (i.e., grey, yellow, green, red, blue, brown, purple and black) were deployed in a randomized complete block design at 16 sites in northern Italy in 2019. A total of 6,001 individuals from 56 longhorn beetle species were trapped. In general, yellow and blue traps caught a significantly higher number of longhorn beetle species than black traps. In addition, trap color significantly affected species richness and abundance at the subfamily and species level, with mixed response mostly linked to the habit of visiting flowers for food. Flower-visiting longhorn beetles mainly exhibited clear preference for flower-related colors, i.e., yellow, green and blue, whereas non-flower-visiting species were more attracted by dark and long-wavelength-dominated colors, like red and brown. Our results clearly indicate that generic surveillance programs should not rely exclusively on black traps and that the use of more trap colors can strongly improve the chance of detecting native and exotic longhorn beetles potentially moved with trades.

Determination of enantiomeric excess by chiral liquid chromatography without enantiomerically pure starting standards

Biomedical Chromatography ◽

10.1002/bmc.2685 ◽

2012 ◽

Vol 26 (10) ◽

pp. 1241-1246 ◽

Cited By ~ 16

Author(s):

F. G. Sánchez ◽

A. Navas Díaz ◽

E. Sánchez Torreño ◽

A. Aguilar ◽

I. Medina Lama ◽

...

Keyword(s):

Liquid Chromatography ◽

Enantiomeric Excess ◽

Stereoselective Synthesis of Quinolizidine Alkaloids: (–)-Lasubin II

Zeitschrift für Naturforschung B ◽

10.1515/znb-2008-0409 ◽

2008 ◽

Vol 63 (4) ◽

pp. 425-430 ◽

Cited By ~ 7

Author(s):

Markus Weymann ◽

Horst Kunz

Keyword(s):

Mannich Reaction ◽

Pure Form ◽

Quinolizidine Alkaloids ◽

Enantiomerically Pure ◽

Quinolizidine Alkaloid

AbstractBased on a higly diastereoselective Mannich reaction of N-(3,4-dimethoxybenzylidene) 2,3,4,6- tetra-O-pivaloyl-β -D-galactopyranosylamine 3 with the Danishefsky diene the quinolizidine alkaloid lasubin II was synthesized in enantiomerically pure form in six steps.