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Volumn 11, Issue 5, 2009, Pages 1051-1054

Synthesis of pyrrolnitrin and related halogenated phenylpyrroles

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; ANTIFUNGAL AGENT; HALOGENATED HYDROCARBON; NITROBENZENE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLNITRIN;

EID: 64349115739     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8026957     Document Type: Article
Times cited : (38)

References (30)
  • 10
    • 64349112601 scopus 로고    scopus 로고
    • 12 in E. coli has been reported, but enzyme activity has only been reconstituted in vitro for PrnA and PrnD.
    • 12 in E. coli has been reported, but enzyme activity has only been reconstituted in vitro for PrnA and PrnD.
  • 15
    • 64349111767 scopus 로고    scopus 로고
    • 3-Chloropyrrole has been isolated and characterized from mixtures obtained upon acidification of N-chloropyrrole (De Rosa, M. J. Org. Chem. 1982, 47, 1008-1010) and photolysis of 3-chloropyridine N-oxide (Bellamy, F.; Streith, J.; Fritz, H. Nouv. J. Chim. 1979, 3, 115-122).
    • 3-Chloropyrrole has been isolated and characterized from mixtures obtained upon acidification of N-chloropyrrole (De Rosa, M. J. Org. Chem. 1982, 47, 1008-1010) and photolysis of 3-chloropyridine N-oxide (Bellamy, F.; Streith, J.; Fritz, H. Nouv. J. Chim. 1979, 3, 115-122).
  • 18
    • 64349111352 scopus 로고    scopus 로고
    • 2 gave complex product mixtures.
    • 2 gave complex product mixtures.
  • 24
    • 64349103672 scopus 로고    scopus 로고
    • While some lithium-halogen exchange does occur at this temperature, the desired 2-bromo-6-iodobenzoic acid is the major product, formed in a 5:1 ratio with the 3-bromobenzoic acid arising from initial lithiumhalogen exchange
    • While some lithium-halogen exchange does occur at this temperature, the desired 2-bromo-6-iodobenzoic acid is the major product, formed in a 5:1 ratio with the 3-bromobenzoic acid arising from initial lithiumhalogen exchange.
  • 25
    • 84985581059 scopus 로고    scopus 로고
    • Compound 3 has been prepared biosynthetically from 7-chlorotryptophan as in van Pee, K.-H.; Salcher, O.; Lingens, F. Angew. Chem.. Intl. Ed. 1980, 19, 828-829.
    • Compound 3 has been prepared biosynthetically from 7-chlorotryptophan as in van Pee, K.-H.; Salcher, O.; Lingens, F. Angew. Chem.. Intl. Ed. 1980, 19, 828-829.
  • 26
    • 0035906509 scopus 로고    scopus 로고
    • Compound 32 has been prepared by reductive dechlorination of 5 with iodotrimethylsilane. See: Sako, M.; Kihara, T.; Okada, K.; Ohtani, Y.; Kawamoto, H. J. Org. Chem. 2001, 66, 3610-3612.
    • Compound 32 has been prepared by reductive dechlorination of 5 with iodotrimethylsilane. See: Sako, M.; Kihara, T.; Okada, K.; Ohtani, Y.; Kawamoto, H. J. Org. Chem. 2001, 66, 3610-3612.
  • 28
    • 0019417895 scopus 로고    scopus 로고
    • Compounds 27 and 29 have been synthesized with tritium at the 2-position of the pyrrole ring using methods similar to those described in ref 8. See: Chang, C. J.; Floss, H. G.; Hook, D. J.; Mabe, J. A.; Manni, P. E.; Martin, L. L.; Schroder, K.; Shieh, T. L. J. Antibiot. 1981, 34, 555-566.
    • Compounds 27 and 29 have been synthesized with tritium at the 2-position of the pyrrole ring using methods similar to those described in ref 8. See: Chang, C. J.; Floss, H. G.; Hook, D. J.; Mabe, J. A.; Manni, P. E.; Martin, L. L.; Schroder, K.; Shieh, T. L. J. Antibiot. 1981, 34, 555-566.
  • 29
    • 64349117650 scopus 로고    scopus 로고
    • Compound 36 has been prepared using methods similar to those described in ref 8. See: UmioS. Kariyone K. Tanaka K. Ueda I. Morimoto Y. Chem. Pharm. Bull. 196977588595.
    • Compound 36 has been prepared using methods similar to those described in ref 8. See: UmioS. Kariyone K. Tanaka K. Ueda I. Morimoto Y. Chem. Pharm. Bull. 196977588595.
  • 30
    • 0021018442 scopus 로고    scopus 로고
    • Compound 4 has been obtained by reduction of 5 as in: van Pee, K.-H.; Salcher, O.; Fischer, P.; Bokel, M.; Lingens, F. J. Antibiot. 1983, 36, 1735-1742.
    • Compound 4 has been obtained by reduction of 5 as in: van Pee, K.-H.; Salcher, O.; Fischer, P.; Bokel, M.; Lingens, F. J. Antibiot. 1983, 36, 1735-1742.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.