2015
DOI: 10.1007/s12039-015-0823-0
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Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

Abstract: Eighteen racemic β-aryl-γ -lactones derived from simple aromatic aldehydes have been obtained in the chemical synthesis. Iodolactones (5c and 6c) were synthesized from (E)-4-(benzo [d][1 ,3 ]-dioxol-5 -yl)-but-3-en-2-one (1). Reductive dehalogenation of iodolactones 5a-c and 6a-c afforded γ -ethyl-γ -lactones (7a-c, 8a-c) whereas the unsaturated lactones (9a-c, 10a-c) were obtained by dehydrohalogenation of iodolactones. All synthesized lactones were fully characterized by spectroscopic data (NMR, IR, HRMS) an… Show more

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Cited by 13 publications
(20 citation statements)
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“…This alcohol was obtained earlier by Skrobiszewski et al as a starting material in the synthesis of racemic hydroxylactones with antifeedant activity. 31 Alcohols 5 and 6 were also treated with acetyl chloride and propionyl chloride to afford racemic acetates 7a,8a and propionates 7b,8b (Scheme 1), not reported previously, which were necessary as the standards for chiral gas chromatography.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…This alcohol was obtained earlier by Skrobiszewski et al as a starting material in the synthesis of racemic hydroxylactones with antifeedant activity. 31 Alcohols 5 and 6 were also treated with acetyl chloride and propionyl chloride to afford racemic acetates 7a,8a and propionates 7b,8b (Scheme 1), not reported previously, which were necessary as the standards for chiral gas chromatography.…”
Section: Resultsmentioning
confidence: 99%
“…31 36À38°C); spectroscopic data consistent with those reported in the literature. 31 4.5. General procedure for the synthesis of racemic acetates 7a,8a and propionates 7b,8b…”
Section: General Procedures For the Claisen-schmidt Condensation Of Almentioning
confidence: 99%
“…Sensory properties make them useful in the production of cosmetics and in the food industry,w here they are responsible for the smell and taste of many products. [21] An important property of lactones is the deterrent ac-tivity, [22][23][24][25][26][27] which can be utilized in the productiono fi nsectcontrol agents.…”
Section: Introductionmentioning
confidence: 99%
“…Also catalyzed by metal triflates [Hf(OTf) 4 in this case],C ollins and co-workersr eported efficient direct macrolactonization of seco acids in high yield without hydrolysis, even in the presence of excess water,f orming av ariety of macrolactones and benzolactones( 55-90 %). [12] The ring of macrolides is contracted when Lewis acidic metal triflates are used as catalysts. [1b] Previousr eports have verified that metal triflates are efficient catalysts for the ring-opening and polymerization of lactones, [10] and our earlier research involved ring-opening poly-merization,r ing-closing depolymerization, and ring contraction by rearrangemento fl actones in the presence of W(OTf) 6 ,a lbeit without as ystematic study.…”
mentioning
confidence: 99%
“…[3b] Macrolidesa re mainly secondary metabolites of bacteria and fungi, whicha re abundant in nature. [12] The ring of macrolides is contracted when Lewis acidic metal triflates are used as catalysts. Further expansion of the substrate scope to include terminal hydroxyfatty acids affords ag reen,s imple, and highly atom-economical method to synthesize g-lactones was developed with the ionic liquid [EMIM]OTf as the solvent.…”
mentioning
confidence: 99%