Stereoselective synthesis of key intermediates for the preparation of strobilurins

Grigorieva, N. Ya.; Smirnov, A. G.; Popovsky, V. A.; Степанов, А. В.

doi:10.1016/j.mencom.2008.03.010

Cited by 6 publications

(5 citation statements)

References 9 publications

(9 reference statements)

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“…Compound G 7 showed 44.67% of higher antifungal activities against Gibberella zeae than kresoxim-methyl. Compounds G 7 and G 8 also showed potent antifungal activities against Rhizoctorua solani, which had high activities as compared to kresoxim-methyl.…”

Section: Antifungal Bioactivity Bioassaymentioning

confidence: 95%

“…The result of preliminary screening is demonstrated in Table 4. Compounds G 5 , G 6 , G 7 and G 8 showed potent antifungal activities of inhibition rate of 23.13%, 32.46%, 35.07% and 20.15%, respectively against Botrytis cinerea Pers growth. But antifungal activities of compounds G 5 , G 6 , G 7 and G 8 were lower than those of kresoxim-methyl and carbendazim.…”

Section: Antifungal Bioactivity Bioassaymentioning

confidence: 99%

“…Compounds G 5 , G 6 , G 7 and G 8 showed potent antifungal activities of inhibition rate of 23.13%, 32.46%, 35.07% and 20.15%, respectively against Botrytis cinerea Pers growth. But antifungal activities of compounds G 5 , G 6 , G 7 and G 8 were lower than those of kresoxim-methyl and carbendazim. Compound G 7 showed 44.67% of higher antifungal activities against Gibberella zeae than kresoxim-methyl.…”

Section: Antifungal Bioactivity Bioassaymentioning

confidence: 99%

“…Their structures were identified by spectrum data. In antifungal bioassays, the title compounds G 5 , G 6 , G 7 and G 8 showed relatively high antifungal activities against Botrytis cinerea Pers, G 7 against Gibberella zeae and G 7 , G 8 against Rhzoctorua solani.…”

Section: Synthesis Of Title Compounds G 1 -G 10mentioning

confidence: 99%

“…These synthetic fungicides are active ingredients with similar action to the natural strobilurin A, which is produced by different wood-rotting fungi. [7][8][9][10] The fungicidal strobilurins display their inhibitory effect on the mitochondrial respiration by binding at the ubiquinol-oxidation centre (Qo-site) of the bc1-enzyme complex (complex III) of a fungus where electron transfer can take place. 2,11 Their wide application prospects make it very important to design and synthesize similar compounds with higher biological activity.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antifungal Bioactivity of Methyl 2‐Methoxyimino‐ 2‐{2‐[(substituted benzylidene)aminooxymethyl]phenyl}acetate and 2‐Methoxyimino‐2‐{2‐[(substituted benzylidene)aminooxy‐ methyl]phenyl}‐N‐methylacetamide Derivatives

Li¹,

Yang²

2009

Chin. J. Chem.

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Ten methyl 2-methoxyimino-2-{2-[(substituted benzylidene)aminooxymethyl]phenyl}acetate and 2-methoxyimino-2-{2-[(substituted benzylidene)aminooxymethyl]phenyl}-N-methylacetamide derivatives were synthesized. Structures of the new compounds were characterized by IR, 1 H NMR and GC-MS data. These compounds at 10 µg/mL were tested in vitro against five pathogenic fungi, namely, Sclerotonia, Botrytis cinerea Pers, Gibberella zeae, Rhizoctorua solani and Pyricularia oryzae. Compounds G 5 , G 6 , G 7 and G 8 showed potent antifungal activities against Botrytis cinerea Pers, G 7 against Gibberella zeae and G 7 , G 8 against Rhizoctorua solani, respectively.

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Section: Antifungal Bioactivity Bioassaymentioning

confidence: 95%

Section: Antifungal Bioactivity Bioassaymentioning

confidence: 99%

Section: Antifungal Bioactivity Bioassaymentioning

confidence: 99%

Section: Synthesis Of Title Compounds G 1 -G 10mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antifungal Bioactivity of Methyl 2‐Methoxyimino‐ 2‐{2‐[(substituted benzylidene)aminooxymethyl]phenyl}acetate and 2‐Methoxyimino‐2‐{2‐[(substituted benzylidene)aminooxy‐ methyl]phenyl}‐N‐methylacetamide Derivatives

Li¹,

Yang²

2009

Chin. J. Chem.

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Highly stereoselective synthesis of 2,5-disubstituted (E, E)-penta-2,4-dienals

et al. 2009

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Stereocontrolled synthesis of (3Z,5E)-6-aryl-3-methylhexa-3,5-dien-1-ols, intermediates in the synthesis of strobilurin antibiotics

et al. 2010

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2E,4E) 5 Aryl 2 (2 benzyloxyethyl)penta 2,4 dien 1 als (aryl is phenyl and 4 methox yphenyl) were reduced with NaBH 4 quantitatively and stereospecifically to the corresponding penta 2(E),4(E) dien 1 ols. The hydroxymethyl group in the latter was transformed into a methyl one with a stereoselectivity of 92-97%. Debenzylation of the resulting (1E,3Z) 1 aryl 6 benzyloxy 4 methylhexa 1,3 dienes with AlCl 3 in the presence of PhNMe 2 afforded the target (3Z,5E) 6 aryl 3 methylhexa 3,5 dien 1 ols; the configuration of the C=C bonds in the con jugated aryl diene systems was retained at 95%.

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Stereoselective synthesis of key intermediates for the preparation of strobilurins

Cited by 6 publications

References 9 publications

Synthesis and Antifungal Bioactivity of Methyl 2‐Methoxyimino‐ 2‐{2‐[(substituted benzylidene)aminooxymethyl]phenyl}acetate and 2‐Methoxyimino‐2‐{2‐[(substituted benzylidene)aminooxy‐ methyl]phenyl}‐N‐methylacetamide Derivatives

Synthesis and Antifungal Bioactivity of Methyl 2‐Methoxyimino‐ 2‐{2‐[(substituted benzylidene)aminooxymethyl]phenyl}acetate and 2‐Methoxyimino‐2‐{2‐[(substituted benzylidene)aminooxy‐ methyl]phenyl}‐N‐methylacetamide Derivatives

Highly stereoselective synthesis of 2,5-disubstituted (E, E)-penta-2,4-dienals

Stereocontrolled synthesis of (3Z,5E)-6-aryl-3-methylhexa-3,5-dien-1-ols, intermediates in the synthesis of strobilurin antibiotics

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