Volatile Lactones — (5S,S)‐5‐Methyl‐3‐(methylalkyl)furan‐2(5H)‐ones — Identified in the Submerged Cultivation of Streptomyces Avermitilis

Řezanka, Tomáš; Sigler, Karel

doi:10.1002/ejoc.200600343

Cited by 11 publications

(15 citation statements)

References 45 publications

(57 reference statements)

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“…According to MS, we identified another homologous series, viz. 3-methyl-, 3-ethyl-, 3-propyl-, 3-butyl-, 3-hexyl-, 3-isohexyl-and 3-heptyl-5-methyl-3-oxol-2-one (Table I); some of the unidentified peaks in the chromatographic profile can be attributed to new and/or as yet unknown oxolone derivatives (see Řezanka and Sigler 2006). While the production of geosmin is characterized by earthy smell, the presence of oxolones can be easily identified as a musty or dank smell.…”

Section: Resultsmentioning

confidence: 98%

“…By using the GC-MS and other chemical-physical methods, these compounds were determined to be 5(S)-methyl-3(S)-(methylalkyl)furan-(5H)-2-ones. This study thus documented for the first time the existence of volatile lactones with an anteiso structure of the side chain (Řezanka and Sigler 2006). Banskota et al (2006) reported on three new 5-alkenyl-3,3(2H)-furanones from two Streptomyces species.…”

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confidence: 96%

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Identification of odorous compounds from nine fermentor-cultivated Streptomyces strains

2008

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The chemical composition was determined of odors produced by nine strains of streptomycetes (Streptomyces aureofaciens, S. avermitilis, S. cinnamonensis, S. coelicolor, S. griseus, S. lividans, S. rimosus, S. spectabilis, S. virginiae) cultivated in a fermentor under similar cultivation conditions. GC-MS analysis identified more than twenty noteworthy volatile chemical individuals. The main components of the odor spectrum were geosmin and unique homologues of oxolones (dihydrofuranones), minor compounds included, e.g., pyrazine derivatives, acetoin and its homologues, aromatic esters, furan derivatives.

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Section: Resultsmentioning

confidence: 98%

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confidence: 96%

Identification of odorous compounds from nine fermentor-cultivated Streptomyces strains

2008

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“…[15] With phosphonium salts in hand, we next studied the synthesis of aldehydes 22-24 (Scheme 3). The protection of 1,9-nonanediol (13) with benzyl chloride produced 9-(benzyloxy)nonan-1-ol ( 14), [16] followed by the oxidation with Dess-Martin periodinane to afford benzyloxy aldehyde 15. [17,18] In the presence of n-butyllithium, Wittig coupling of 9-(benzyloxy)nonanal (15) with phosphonium salt 10 led to the desired olefinic ether 16 (96 % yield, Z : E = 98 : 2, determined by 13 C NMR spectra).…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of Contact Pheromone Component of Xylotrechus colonus and Its Analogues

Yuan

et al. 2023

ChemistrySelect

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Xylotrechus colonus is an abundant wood‐boring pest of woody plants. 3‐Methylpentacosane was identified as the component of its contact pheromone. A novel and efficient asymmetric synthesis of (S)‐3‐methylpentacosane and its analogues was developed using (S)‐2‐methylbutan‐1‐ol as chiral source. The key of this approach included Wittig coupling of chiral phosphonium salt with aldehyde, Pd‐catalyzed hydrogenation and Appel reaction. Our synthesis would be helpful for the control and detect of this pest.

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“…Optical rotations were determined with a PerkinElmer Model 241 MC polarimeter. IR spectra were recorded on an IR spectrum One (PE) spectrometer, and 1 H NMR (600 MHz) and 13 C NMR (150 MHz) spectra were recorded on a Varian Unity INOVA 600 spectrometer in CDCl 3 using TMS as internal standard. The diastereoisomeric purity was determined by means of HPLC (Dionex, Ultimate3000 pump) using solid-phase extraction in reversed phase mode (C8 phase) (70:30 water-methanol, 1 mL/min, 254 nm).…”

Section: Methodsmentioning

confidence: 99%

Stereoselective synthesis of an alarm pheromone of Grematogaster ants using (4S)-4-benzyloxazolidinone as chiral auxiliary

Zhou

Chen

et al. 2010

Chem Nat Compd

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547.72.74 (S)-6-Methyl-3-octanone, a component of the alarm pheromone of Grematogaster ants, was synthesized through a key step of stereoselective Michael addition reaction using (4S)-4-benzyloxazolidinone as chiral auxiliary. The target product was obtained with an overall yield of 43.0% over six steps in high enantiomeric purity.Several insects show a remarkable ability to distinguish the stereoisomers of their chiral pheromone components [1]. For instance, specificity of response to the enantiomers of their alarm pheromones has been demonstrated for the leaf cutting ants, Atta texana and Atta cephalotes, and the myrmicine ant, Pogonomyrmex barbatus. 6-Methyl-3-octanone was isolated and identified as a component of the alarm pheromone of Grematogaster ants [2], a pest causing serious losses of croppers throughout the world. Since effective and cost-efficient control of Grematogaster ant populations can be foreseen with the aid of the alarm pheromone, several total syntheses of the racemate and the (R) enantiomer or (S) enantiomer have been published [2][3][4][5].Recently, our group has undertaken a research program on preparation of chiral auxiliaries [6-8] and application of them to synthesize the insect pheromones [9,10]. In this paper, we have developed an efficient procedure to stereoselectively synthesize (S)-6-methyl-3-octanone (1) via a key step of asymmetric Michael addition using optically pure (4S)-4-benzyloxazolidinone as chiral auxiliary (Scheme 1).

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Volatile Lactones — (5S,S)‐5‐Methyl‐3‐(methylalkyl)furan‐2(5H)‐ones — Identified in the Submerged Cultivation of Streptomyces Avermitilis

Cited by 11 publications

References 45 publications

Identification of odorous compounds from nine fermentor-cultivated Streptomyces strains

Identification of odorous compounds from nine fermentor-cultivated Streptomyces strains

Asymmetric Synthesis of Contact Pheromone Component of Xylotrechus colonus and Its Analogues

Stereoselective synthesis of an alarm pheromone of Grematogaster ants using (4S)-4-benzyloxazolidinone as chiral auxiliary

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