A tandem michael reaction-cycloalkylation utilizing 2-nitropropane: a facile route to the acid component of insecticidal pyrethroids

Babler, James H.; Spina, Kenneth P.

doi:10.1016/s0040-4039(00)98342-4

Cited by 24 publications

(7 citation statements)

References 19 publications

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“…Natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum) have the synthetic analog pyrethroid, which now constitutes a major proportion of the synthetic insecticides. 17 A large number of known drugs arise from the reduction of appropriate precursors (α,β-unsaturated carboxylic acids), for example, Ariflo, 18 an orally active second-generation phosphodiesterase type 4 inhibitor (PDE4) inhibitor for the treatment of asthma, as well as non-steroidal anti-inflammatory drugs, such as ibuprofen 19 and naproxen. 20…”

Section: Introductionmentioning

confidence: 99%

Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids

Vitnik

Milenkovic

Dilber

et al. 2012

JSCS

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A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. Antimicrobial activity was evaluated using broth microdilution method. All acids 1-12 exhibit a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with TEBA as catalyst

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Section: Introductionmentioning

confidence: 99%

Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids

Vitnik

Milenkovic

Dilber

et al. 2012

JSCS

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“…To test the generality of the reaction and also to understand the substituent effect on the reaction, a number of racemic trans -3-aryl-2,2-dimethylcyclopropanecarbonitriles 1b − h were synthesized and subjected to Rhodococcus sp. AJ270.…”

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confidence: 99%

“…Encouraged by the abovementioned results, we then tested the biotransformation of racemic cis -2,2-dimethyl-3-arylcyclopropanecarbonitriles 4 . In sharp contrast to an effective biotransformation of racemic trans -2,2-dimethyl-3-arylcyclopropanecarbonitriles 1 , no hydrolysis of nitriles 4 was observed under the same conditions.…”

mentioning

confidence: 99%

Nitrile Biotransformation for Highly Enantioselective Synthesis of 3-Substituted 2,2-Dimethylcyclopropanecarboxylic Acids and Amides

Wang

Feng

2002

J. Org. Chem.

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Biotransformations of differently configured 2,2-dimethyl-3-substitued-cyclopropanecarbonitriles were studied using a nitrile hydratase/amidase-containing Rhodococcus sp. AJ270 whole-cell catalyst under very mild conditions. Although all of the cis-3-aryl-2,2-dimethylcyclopropanecarbonitriles appeared inert toward the biocatalyst, a number of racemic trans-isomers efficiently underwent a highly enantioselective hydrolysis to produce (+)-(1R,3R)-3-aryl-2,2-dimethylcyclopropanecarboxylic acids and (-)-(1S,3S)-3-aryl-2,2-dimethylcyclopropanecarboxamides in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of 1R-enantioselective nitrile hydratase and amidase, with the later being a dominant factor. The influence of the substrates on both reaction efficiency and enantioselectivity was discussed in terms of steric and electronic effects. Coupled with chemical transformations, biotransformations of nitriles provided convenient syntheses of optically pure geminally dimethyl-substituted cyclopropanecarboxylic acids and amides, including chrysanthemic acids, in both enantiomeric forms.

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“…27 Compound 7 was converted to an isocyanate by Curtius rearrangement with DPPA and the HCl salt of compound 6 added to the reaction mixture to form the urea linkage. Finally, hydrolysis of the ester group under standard basic conditions provided the target compound 8.…”

Section: B S T R a C Tmentioning

confidence: 99%

Three-dimensional rational approach to the discovery of potent substituted cyclopropyl urea soluble epoxide hydrolase inhibitors

Takai

Chiyo

Nakajima

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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A tandem michael reaction-cycloalkylation utilizing 2-nitropropane: a facile route to the acid component of insecticidal pyrethroids

Cited by 24 publications

References 19 publications

Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids

Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids

Nitrile Biotransformation for Highly Enantioselective Synthesis of 3-Substituted 2,2-Dimethylcyclopropanecarboxylic Acids and Amides

Three-dimensional rational approach to the discovery of potent substituted cyclopropyl urea soluble epoxide hydrolase inhibitors

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