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Volumn 46, Issue 11, 1998, Pages 4748-4753

Isolation of N-(2-Methyl-3-oxodecanoyl)pyrrole and N-(2-Methyl-3-oxodec-8-enoyl)pyrrole, Two New Natural Products from Penicillium brevicompactum, and Synthesis of Analogues with Insecticidal and Fungicidal Activity

Author keywords

2 (3 oxoacyl)pyrrole; Fungal metabolites; Fungicide; Insecticide; Meldrum's acid; Penicillium brevicompactum

Indexed keywords

PENICILLIUM BREVICOMPACTUM;

EID: 0000250492     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9800763     Document Type: Article
Times cited : (19)

References (27)
  • 4
    • 0001318231 scopus 로고
    • Three piperazinediones and a drimane diterpenoid from
    • Ayer, W. A.; Altena, I. V.; Browne, L. M. Three piperazinediones and a drimane diterpenoid from. Phytochemistry 1990, 29 (5), 1661-1665.
    • (1990) Phytochemistry , vol.29 , Issue.5 , pp. 1661-1665
    • Ayer, W.A.1    Altena, I.V.2    Browne, L.M.3
  • 5
    • 11944265303 scopus 로고
    • Mastering β-Keto Esters
    • Benetti, S.; Romagnoli, R. Mastering β-Keto Esters. Chem. Rev. 1995, 95, 1065-1114.
    • (1995) Chem. Rev. , vol.95 , pp. 1065-1114
    • Benetti, S.1    Romagnoli, R.2
  • 6
    • 0000775710 scopus 로고
    • Studies in relation to biosynthesis-XLIV. Structural elucidations of Brevianamides-B, -C, -D, and -F
    • Birch, A. J.; Russell, F. A. Studies in relation to biosynthesis-XLIV. Structural elucidations of Brevianamides-B, -C, -D, and -F. Tetrahedron 1972, 28, 2999-3002.
    • (1972) Tetrahedron , vol.28 , pp. 2999-3002
    • Birch, A.J.1    Russell, F.A.2
  • 7
    • 0014786230 scopus 로고
    • The structural elucidation ana some aspects of the biosynthesis of Brevianamides A and E
    • Birch, A. J.; Wright, J. J. The structural elucidation ana some aspects of the biosynthesis of Brevianamides A and E. Tetrahedron 1970, 26, 2329-2344.
    • (1970) Tetrahedron , vol.26 , pp. 2329-2344
    • Birch, A.J.1    Wright, J.J.2
  • 8
    • 0000190025 scopus 로고
    • The molecular constitution of micophenolic acid, a metabolic product of Penicillium brevicompactum
    • Birkinshaw, J. F.; Raistrick, H.; Ross, D. J. The molecular constitution of micophenolic acid, a metabolic product of Penicillium brevicompactum. Biochem. J. 1952, 50, 630-634.
    • (1952) Biochem. J. , vol.50 , pp. 630-634
    • Birkinshaw, J.F.1    Raistrick, H.2    Ross, D.J.3
  • 9
    • 0001471258 scopus 로고
    • Insecticidal action and mitochondrial uncoupling activity of AC-303,630 and related halogenated pyrroles
    • Black, B. C.; Hollingworth, R. M.; Ahammdsahib, K. I.; Kukel, C. D.; Donovan, S. Insecticidal action and mitochondrial uncoupling activity of AC-303,630 and related halogenated pyrroles. Pestic. Biochem. Physiol. 1994, 50, 115-128.
    • (1994) Pestic. Biochem. Physiol. , vol.50 , pp. 115-128
    • Black, B.C.1    Hollingworth, R.M.2    Ahammdsahib, K.I.3    Kukel, C.D.4    Donovan, S.5
  • 10
    • 0017067458 scopus 로고
    • Discovery of insect anti-juvenile hormones in plants
    • Bowers, W. S.; Ohta, T.; Cleere, J. S.; Marsella, P. A. Discovery of insect anti-juvenile hormones in plants. Science 1976, 193, 542-547.
    • (1976) Science , vol.193 , pp. 542-547
    • Bowers, W.S.1    Ohta, T.2    Cleere, J.S.3    Marsella, P.A.4
  • 11
    • 0016913421 scopus 로고
    • Cristal and molecular structure of Compactin, a new antifungal metabolite from Penicillium brevicompactum
    • Brown, A. G.; Smale, T. C.; King. T. J.; Kasenkamp, R.; Thompson, R. H. Cristal and molecular structure of Compactin, a new antifungal metabolite from Penicillium brevicompactum. J. Chem. Soc., Perkin. Trans, 1 1976, 1165-1170.
    • (1976) J. Chem. Soc., Perkin. Trans, 1 , pp. 1165-1170
    • Brown, A.G.1    Smale, T.C.2    King, T.J.3    Kasenkamp, R.4    Thompson, R.H.5
  • 12
    • 33947440940 scopus 로고
    • The structure of Meldrum's supposed β-lactonic acid
    • Davidson, D.; Bernhardt, S. A. The structure of Meldrum's supposed β-lactonic acid. J. Am. Chem. Soc. 1948, 70, 3426.
    • (1948) J. Am. Chem. Soc. , vol.70 , pp. 3426
    • Davidson, D.1    Bernhardt, S.A.2
  • 13
    • 0009784925 scopus 로고
    • N-Benzoylphenylalanine and N-Benzoylphenylalaninol and their biosynthesis in Penicillium brevicompactum
    • Doerfler, D. L.; Bird, B. A.; Campbell, I. M. N-Benzoylphenylalanine and N-Benzoylphenylalaninol and their biosynthesis in Penicillium brevicompactum. Phytochemistry 1981, 20, 2303-2304.
    • (1981) Phytochemistry , vol.20 , pp. 2303-2304
    • Doerfler, D.L.1    Bird, B.A.2    Campbell, I.M.3
  • 14
    • 0004116672 scopus 로고
    • Cambridge University Press: Cambridge, England
    • Finney, D. J. Probit Analysis; Cambridge University Press: Cambridge, England, 1971.
    • (1971) Probit Analysis
    • Finney, D.J.1
  • 15
    • 0345186957 scopus 로고
    • Etude du metabolisme ternaire de Penicillium brevicompactum
    • Godin, P. Etude du metabolisme ternaire de Penicillium brevicompactum. Biochim. Biophys. Acta 1955, 11, 114-118.
    • (1955) Biochim. Biophys. Acta , vol.11 , pp. 114-118
    • Godin, P.1
  • 16
    • 0347444841 scopus 로고
    • Insecticidal pyrroles: Synthesis of Bis(trifluoromethyl)pyrroles via rearrangement of O-vinyloximes
    • Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; American Chemical Society: Washington, DC
    • Kameswaran, V.; Addor, R. W.; Ward, R. K. Insecticidal pyrroles: Synthesis of Bis(trifluoromethyl)pyrroles via rearrangement of O-vinyloximes. In Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; ACS Symposium Series 504; American Chemical Society: Washington, DC, 1992; pp 306-312.
    • (1992) ACS Symposium Series 504 , pp. 306-312
    • Kameswaran, V.1    Addor, R.W.2    Ward, R.K.3
  • 17
    • 0006108398 scopus 로고
    • Insecticidal pyrroles: Arylpyrrolecarbonitriles incorporating a trifluoromethyl group
    • Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; American Chemical Society: Washington, DC
    • Kuhn, D. G.; Kamhi, V. M.; Furch, J. A.; Diehl, R. E.; Trotto, S. H.; Lowen, G. T.; Babcock, T. J. Insecticidal pyrroles: arylpyrrolecarbonitriles incorporating a trifluoromethyl group. In-Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; ACS Symposium Series 504; American Chemical Society: Washington, DC, 1992; pp 298-305.
    • (1992) ACS Symposium Series 504 , pp. 298-305
    • Kuhn, D.G.1    Kamhi, V.M.2    Furch, J.A.3    Diehl, R.E.4    Trotto, S.H.5    Lowen, G.T.6    Babcock, T.J.7
  • 18
    • 0343404767 scopus 로고
    • Synthesis of fungicidal pheylpyrroles
    • Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; American Chemical Society: Washington, DC
    • Kuppel, P. C.; Lantzsch, R.; Wollweber, D. Synthesis of fungicidal pheylpyrroles. In Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; ACS Symposium Series 504; American Chemical Society: Washington, DC, 1992; pp 405-413.
    • (1992) ACS Symposium Series 504 , pp. 405-413
    • Kuppel, P.C.1    Lantzsch, R.2    Wollweber, D.3
  • 19
    • 0344324490 scopus 로고
    • Brevigellin, a benzoylated cyclodepsipeptide from Penicillium brevicompactum
    • McCorkindale, N. J.; Baxter, R. L. Brevigellin, a benzoylated cyclodepsipeptide from Penicillium brevicompactum. Tetrahedron 1981, 37, 1795-1801.
    • (1981) Tetrahedron , vol.37 , pp. 1795-1801
    • McCorkindale, N.J.1    Baxter, R.L.2
  • 20
    • 0345619070 scopus 로고
    • The structure and chemistry of pebrolide, desacetylpebrolide and 1-deoxypebrolide, sesquiterpene benzoates from Penicillium bervicompactum
    • McCorkindale, N. J.; Calzadilla, C. H.; Hutchinson, S. A.; Kitson, D. H.; Ferguson, G.; Campbell, I. M. The structure and chemistry of pebrolide, desacetylpebrolide and 1-deoxypebrolide, sesquiterpene benzoates from Penicillium bervicompactum. Tetrahedron 1981, 37, 649-653.
    • (1981) Tetrahedron , vol.37 , pp. 649-653
    • McCorkindale, N.J.1    Calzadilla, C.H.2    Hutchinson, S.A.3    Kitson, D.H.4    Ferguson, G.5    Campbell, I.M.6
  • 23
    • 0002816935 scopus 로고
    • Phenylpyrroles, a new class of agricultural fungicides related to the natural antibiotic Pyrrolnitrin
    • Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; American Chemical Society: Washington, DC
    • Nyfeler, R.; Ackermann, P. Phenylpyrroles, a new class of agricultural fungicides related to the natural antibiotic Pyrrolnitrin. In Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; ACS Symposium Series 504; American Chemical Society: Washington, DC, 1992; pp 395-404.
    • (1992) ACS Symposium Series 504 , pp. 395-404
    • Nyfeler, R.1    Ackermann, P.2
  • 24
    • 0007374717 scopus 로고
    • Meldrum's acid in organic synthesis. A general and versatile synthesis of β-keto esters
    • Oikawa, Y.; Sugano, K.; Yonemitsu, O. Meldrum's acid in organic synthesis. A general and versatile synthesis of β-keto esters. J. Org. Chem. 1978, 43, 2087-2088.
    • (1978) J. Org. Chem. , vol.43 , pp. 2087-2088
    • Oikawa, Y.1    Sugano, K.2    Yonemitsu, O.3
  • 25
    • 0345186958 scopus 로고
    • 3,5-Dihidroxyphthalic acid, a new product of the metabolism of glucose by Penicillium brevicompactum
    • Oxford, A. E.; Raistrick, H. 3,5-Dihidroxyphthalic acid, a new product of the metabolism of glucose by Penicillium brevicompactum. Biochem. J. 1932, 27, 1902-1906.
    • (1932) Biochem. J. , vol.27 , pp. 1902-1906
    • Oxford, A.E.1    Raistrick, H.2
  • 26
    • 0344756666 scopus 로고
    • The molecular constitution of the metabolic products at Penicillium brevicompactum Dierckx and related species
    • Oxford, A. E.; Raistrick, H. The molecular constitution of the metabolic products at Penicillium brevicompactum Dierckx and related species. Biochem. J. 1933, 27, 634-652.
    • (1933) Biochem. J. , vol.27 , pp. 634-652
    • Oxford, A.E.1    Raistrick, H.2
  • 27
    • 0026736879 scopus 로고
    • Aminolyais of 5-acyl-2,2-dimethyl-1,3-dioxane-4,6-diones (acyl Meldrum's acids) as a versatile method for the synthesis of β-oxo carboxamides
    • Pakr, C. S.; Yang, H, C,; Choi, E. B. Aminolyais of 5-acyl-2,2-dimethyl-1,3-dioxane-4,6-diones (acyl Meldrum's acids) as a versatile method for the synthesis of β-oxo carboxamides. Synthesis 1992, 1213-1214.
    • (1992) Synthesis , pp. 1213-1214
    • Pakr, C.S.1    Yang, H.C.2    Choi, E.B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.