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Volumn 124, Issue 44, 2002, Pages 12950-12951

Enantioselective synthesis of the bromopyrrole alkaloids manzacidin A and C by stereospecific C-H bond oxidation

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALPHA ADRENERGIC RECEPTOR BLOCKING AGENT; MANZACIDIN A; MANZACIDIN B; MANZACIDIN C; NATURAL PRODUCT; SEROTONIN ANTAGONIST; UNCLASSIFIED DRUG;

EID: 0037032211     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028139s     Document Type: Article
Times cited : (180)

References (25)
  • 7
    • 0033574470 scopus 로고    scopus 로고
    • Substituted 3,4,5,6-tetrahydropyrimidines are structural components of certain bacterial siderophores, see: (a) Zamri, A.; Sirockin, F.; Abdallah, M. A. Tetrahedron 1999, 55, 5157-5170. (b) Jones, R. C. F.; Crockett, A. K. Tetrahedron Lett. 1993, 34, 7459-7462.
    • (1999) Tetrahedron , vol.55 , pp. 5157-5170
    • Zamri, A.1    Sirockin, F.2    Abdallah, M.A.3
  • 8
    • 0027527461 scopus 로고
    • Substituted 3,4,5,6-tetrahydropyrimidines are structural components of certain bacterial siderophores, see: (a) Zamri, A.; Sirockin, F.; Abdallah, M. A. Tetrahedron 1999, 55, 5157-5170. (b) Jones, R. C. F.; Crockett, A. K. Tetrahedron Lett. 1993, 34, 7459-7462.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7459-7462
    • Jones, R.C.F.1    Crockett, A.K.2
  • 12
    • 0000619305 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin
    • For comprehensive reviews on catalytic asymmetric hydrogenation, see: (a) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 1, pp 122-182. (b) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 122-182
    • Brown, J.M.1
  • 13
    • 0000458209 scopus 로고
    • For comprehensive reviews on catalytic asymmetric hydrogenation, see: (a) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 1, pp 122-182. (b) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
    • (1993) Chem. Rev. , vol.93 , pp. 1307-1370
    • Hoveyda, A.H.1    Evans, D.A.2    Fu, G.C.3
  • 14
    • 0034706033 scopus 로고    scopus 로고
    • Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943. For a recent review of the asymmetric carbonyl ene reaction, see: Mikami, K.; Nakai, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 543-568.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7936-7943
    • Evans, D.A.1    Tregay, S.W.2    Burgey, C.S.3    Paras, N.A.4    Vojkovsky, T.5
  • 15
    • 0034706033 scopus 로고    scopus 로고
    • Ojima, I., Ed.; Wiley-VCH: New York
    • Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943. For a recent review of the asymmetric carbonyl ene reaction, see: Mikami, K.; Nakai, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 543-568.
    • (2000) Catalytic Asymmetric Synthesis , pp. 543-568
    • Mikami, K.1    Nakai, T.2
  • 17
    • 0005174020 scopus 로고    scopus 로고
    • note
    • 2OTf and (R,R)-Et-DUPHOS reverses product selectivity, but gives only a 60:40 mixture of 6a/6c.
  • 18
    • 0005138525 scopus 로고    scopus 로고
    • note
    • In practice, we have found that separation is more easily accomplished following sulfamate ester insertion.
  • 24
    • 0005202490 scopus 로고    scopus 로고
    • note
    • D = -28° (c = 0.67, MeOH).
  • 25
    • 0005138775 scopus 로고    scopus 로고
    • note
    • D = +37° (c = 0.23, MeOH)). This discrepancy may be attributed to impurities in natural 1c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.