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Synthetic scheme for total synthesis of Chrysanthemic Acid

T1 - Non-head-to-tail monoterpenes. Synthesis of (S)-lyratol and (S)-lyratyl acetate from (1R,3R)-chrysanthemic acid

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Synthesis of (IR)-(+)--chrysanthemic acid - ResearchGate

Pyrethroid esters on the basis of (1R)-trans-chrysanthemic acid are characterized by the combination of high biological activity with very low toxicity for mammals, which makes them extremely perspective as indoor domestic insecticides. In general case, pyrethroid esters of (1R)-trans-chrysanthemic acid exceed the esters of (1R)-cis-chrisanthemic acid in insecticide activity; however, (1R)-cis-chrisanthemates appear to be more active in respect of some objects (e.g.: mosquitos). Therefore, the development of convenient synthetic methods of (1R)-cis-chrisanthemic acids is of special interest. (1R)-cis-nor-chrisanthemic acid is a structural hybrid of (1R)-cis-chrisanthemic and permetrine acids. The obtained pyrethroids combine the properties of both chresanthemates and esters of permethrine acids; in terms of insecticide activity, they are closer to the correspondent derivatives of permethrine acid, but unlike the latter, they are significantly less toxic for fish, which is sure to be their prime advantage.

Chrysanthemic acid synthesis essay - Bascom United …

N2 - (+)-(S)-Lyratol (1-OH) and (+)-(S)-lyratyl acetate (1-OAc) were synthesized from (1R,3R)-chrysanthemic acid ((1R,3R)-2-OH). The key steps in the sequence were the stereospecific oxidation of the (E)-methyl group in the isobutenyl moiety of chrysanthemyl acetate ((1R,3R)-3-OAc) with selenium dioxide and the regiospecific cleavage of the C(1)-C(2) cyclopropane bond in aldehyde methanesulfonate (1R,3R)-4-OMs to give the santolinyl skeleton found in lyratol. Since the synthesis began with (1R,3R)-chrysanthemic acid ((1R,3R)-2-OH) and did not alter the configuration at C(3), (+)-lyratol and (+)-lyratyl acetate are the (S) enantiomers. The absolute configurations of synthetic lyratol and lyratyl acetate are the same as those of their naturally occurring counterparts isolated from Cyanthocline lyrata.

Chrysanthemic acid synthesis essay - …

Synthesis and Insecticidal Activity of Novel Camptothecin Derivatives Containing Analogs of Chrysanthemic Acid Moieties[J].

Field capacityFD fluorescence detectionFDA Food and Drug Administration (USA)FEF forced expiratory flowFEP free erythrocyte porphyrinFEV forced expiratory volumefg femtogram (10-15g)FI flame ionizationFID flame ionization detectorFMLP formyl methionyl leucyl phenylalanineFMN flavin mononucleotideFOB functional observational batteryFPD flame photometric detectorFR flame retardantFS fluorescence spectrophotometryFSC Food Safety Council (USA)FSD flame photometric detector selective for sulfurFSH follicle-stimulating hormoneFTIR Fourier transform infraredFVC forced vital capacityGA gibberillic acidGABA gamma-aminobutyric acidGAG glycosaminoglycanGALT gut-associated lymphoid tissueGAP good agricultural practiceGBM glomerular basement membraneGC gas chromatographyGC-ECD gas chromatography with electron capture detectorGC-SIM gas chromatography with selected ion monitoringGDH glutamate dehydrogenaseGDMS glow discharge mass spectrometryGEMS Global Environmental Monitoring SystemGESAMP Group of Experts for the Scientific Aspects of Marine PollutionGFAAS graphite furnace atomic absorption spectrometryGFR glomerular filtration rateGGT gamma-glutamyltranspeptidaseGH growth hormoneGI gastrointestinalGIFAP International Group of National Association of Manufacturers of Agrochemical Products (French Acronym for: Groupement International des Associations Nationales de Fabricants de Produits Agrochimiques)GLC gas-liquid chromatographyGLDH glutamate dehydrogenaseGLP good laboratory practicecGMP cyclic guanosine monophosphateGOT glutamic-oxaloacetic transaminaseGPC gel permeation chromatographyGPMT guinea-pig maximization testGPT glutamic-pyruvic transaminaseGS glutamine synthetaseGSH glutathione-SHGST glutathione-S-transferaseGTB glomerular tubular balanceGV guidance valueGWP global-warming potentialh hour(s)ha hectareHb haemoglobinHBCD hexabromocyclododecaneHBDH hydroxybutyric dehydrogenaseH & E haematoxolin and eosinHCB hexachlorobenzeneHCBD hexachloro-1,3-butadieneHCFC hydrochlorofluorocarbonHCFH-22 chlorodifluoromethane (CHClF2)HCG human chorionic gonadotropinHCH hexachlorocyclohexaneHDL high density lipoproteinHDPE high density polyethyleneHEAL Human Exposure Assessment LocationHECD Hall electron capture detectorHEV high endothelial venuleHEX hexachlorocyclopentadieneHGPRT hypoxanthine-guanine phosphoribosyltransferaseHIPS high impact polystyreneHIV human immunodeficiency virusHLB hydrophilic-lipophilic balanceHLV hygienic limit valuehnRNA heterogeneous nuclear RNAHPCA human progenitor cell antigenHPI cyclohexane-1,2-dicarboximideHPLC high-performance liquid chromatographyHPTLC high-performance thin-layer chromatographyHQ hydroquinoneHS headspaceHSA heat-stable antigen; human serum albuminHSG Health and Safety GuideIARC International Agency for Research on CancerIC ion chromatographyICAM intercellular adhesion moleculeIC50 median inhibitory concentrationICD International Classification of DiseasesICG indocyanine greenICP inductively coupled plasmaICST isolated cold stress testingi.d.

AB - (+)-(S)-Lyratol (1-OH) and (+)-(S)-lyratyl acetate (1-OAc) were synthesized from (1R,3R)-chrysanthemic acid ((1R,3R)-2-OH). The key steps in the sequence were the stereospecific oxidation of the (E)-methyl group in the isobutenyl moiety of chrysanthemyl acetate ((1R,3R)-3-OAc) with selenium dioxide and the regiospecific cleavage of the C(1)-C(2) cyclopropane bond in aldehyde methanesulfonate (1R,3R)-4-OMs to give the santolinyl skeleton found in lyratol. Since the synthesis began with (1R,3R)-chrysanthemic acid ((1R,3R)-2-OH) and did not alter the configuration at C(3), (+)-lyratol and (+)-lyratyl acetate are the (S) enantiomers. The absolute configurations of synthetic lyratol and lyratyl acetate are the same as those of their naturally occurring counterparts isolated from Cyanthocline lyrata.

Studies on Chrysanthemic Acid: Part V. A Synthesis of …

Last year, most of the groups working on the synthesis of chrysanthemic acid were attempting to use the procedure described by Schatz in the J.

(+)-(S)-Lyratol (1-OH) and (+)-(S)-lyratyl acetate (1-OAc) were synthesized from (1R,3R)-chrysanthemic acid ((1R,3R)-2-OH). The key steps in the sequence were the stereospecific oxidation of the (E)-methyl group in the isobutenyl moiety of chrysanthemyl acetate ((1R,3R)-3-OAc) with selenium dioxide and the regiospecific cleavage of the C(1)-C(2) cyclopropane bond in aldehyde methanesulfonate (1R,3R)-4-OMs to give the santolinyl skeleton found in lyratol. Since the synthesis began with (1R,3R)-chrysanthemic acid ((1R,3R)-2-OH) and did not alter the configuration at C(3), (+)-lyratol and (+)-lyratyl acetate are the (S) enantiomers. The absolute configurations of synthetic lyratol and lyratyl acetate are the same as those of their naturally occurring counterparts isolated from Cyanthocline lyrata.

In order to improve the insecticidal activity of CPT, ten novel camptothecin (1) and 10-hydroxycamptothecin (2) derivatives (1a, 1b, 1c, 1d, 1e; 2a, 2b, 2c, 2d, 2e) were designed and synthesized via esterification with analogs of chrysanthemic acid, which have outstanding insecticidal activity.

Stereospecific Synthesis of Optically Pure (+)--Chrysanthemic Acid from (+)3-Carene     Volume 31 (1967) Issue 1 Pages 33-39
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It is highly toxic to humans, livestock, pets, and wildlife

Chrysanthemic acid is an that is related to a variety of natural and synthetic . It is related to the I and II, as well as the . One of the four , (1,3)- or (+)--chrysanthemic acid (pictured), is the acid part of the ester , which occurs naturally in the seed cases of . Many synthetic pyrethroids, for example the , are esters of all four stereoisomers.

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