ChemInform Abstract: New Synthetic Route to (1R)‐cis‐(‐)‐Permethrin, (1R)‐cis‐(+)‐Cypermethrin and (1R)‐cis‐(+)‐Deltamethrin (Decis) from (+)‐3‐Carene.

Mandal, Amritlal; Borude, D. P.; Armugasamy, R.; Soni, Neetu; Jawalkar, D. G.; Mahajan, S.; Ratnam, Kapila; Goghare, A. D.

doi:10.1002/chin.198710189

Cited by 2 publications

(2 citation statements)

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“…1R-cis-3-(2,2-Dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid was kindly supplied by The Institute of Arable Crops Research (Rothamsted Experimental Station, Long Ashton, U.K.). A number of synthetic routes to this acid are described in the literature (20)(21)(22). Haptens 12 and 13 were made in this laboratory previously (14).…”

Section: Chemicals Andmentioning

confidence: 99%

Enzyme-Linked Immunosorbent Assay for the Pyrethroid Deltamethrin

Lee

Shan

Watanabe

et al. 2002

J. Agric. Food Chem.

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A competitive enzyme-linked immunosorbent assay (ELISA) for the detection of deltamethrin was developed. Two haptens, cyano[3-(4-aminophenoxy)phenyl]methyl 1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate and 3-[(+/-)-cyano[1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropan ecarbonyloxy]methyl]phenoxyacetic acid, were synthesized and conjugated with thyroglobulin as immunogens. Four antisera were generated and screened against six different coating antigens. The assay that was the most sensitive for deltamethrin was optimized and characterized. The I(50) for deltamethrin was 17.5 +/- 3.6 microg/L, and the lower detection limit was 1.1 +/- 0.5 microg/L. This ELISA assay had relatively low cross-reactivities with other major pyrethroids, such as permethrin, phenothrin, bioresmethrin, cyfluthrin, and cypermethrin. Methanol was found to be the best organic cosolvent for this ELISA, with optimal sensitivity observed at a concentration of 40% (v/v). The assay parameters were unchanged at pH values between 5.0 and 8.0, whereas higher ionic strengths strongly suppressed the absorbances. To increase the sensitivity of the overall method, a C(18) sorbent-based solid-phase extraction was used for river water samples. River water samples fortified with deltamethrin were analyzed according to this method. Good recoveries and correlation with spike levels were observed.

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Section: Chemicals Andmentioning

confidence: 99%

Enzyme-Linked Immunosorbent Assay for the Pyrethroid Deltamethrin

Lee

Shan

Watanabe

et al. 2002

J. Agric. Food Chem.

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“…This reaction enabled the stereoselective synthesis of dimethyl cyclopropane 3oxabicyclo[3.1.0]hexan-2-one 5 in 81% ee and 83% isolated yield (Scheme 3a). Further elaboration of this key intermediate via known methods 57,58 can furnish the pyrethroid natural product chrysanthemic acid, permethrin, and phenothrin.…”

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confidence: 99%

Stereodivergent Intramolecular Cyclopropanation Enabled by Engineered Carbene Transferases

2019

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We report the development of engineered myoglobin biocatalysts for executing asymmetric intramolecular cyclopropanations resulting in cyclopropane-fused γ-lactones, which are key motifs found in many bioactive molecules. Using this strategy, a broad range of allyl diazoacetate substrates were efficiently cyclized in high yields with up to 99% enantiomeric excess. Upon remodeling of the active site via protein engineering, myoglobin variants with stereodivergent selectivity were also obtained. In combination with whole-cell transformations, these biocatalysts enabled the gram-scale assembly of a key intermediate useful for the synthesis of the insecticide permethrin and other natural products. The enzymatically produced cyclopropyl-γ-lactones can be further elaborated to furnish a variety of enantiopure trisubstituted cyclopropanes. This work introduces a first example of biocatalytic intramolecular cyclopropanation and provides an attractive strategy for the stereodivergent preparation of fused cyclopropyl-γ-lactones of high value for medicinal chemistry and the synthesis of natural products.

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ChemInform Abstract: New Synthetic Route to (1R)‐cis‐(‐)‐Permethrin, (1R)‐cis‐(+)‐Cypermethrin and (1R)‐cis‐(+)‐Deltamethrin (Decis) from (+)‐3‐Carene.

Abstract: A method for the synthesis of (1R)‐cis‐(‐)‐permethrin (VII) is described, starting from (+)‐3‐carene (I).

Cited by 2 publications

References 1 publication

Enzyme-Linked Immunosorbent Assay for the Pyrethroid Deltamethrin

Enzyme-Linked Immunosorbent Assay for the Pyrethroid Deltamethrin

Stereodivergent Intramolecular Cyclopropanation Enabled by Engineered Carbene Transferases

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