메뉴 건너뛰기




Volumn 36, Issue 6, 1999, Pages 1539-1547

1,3-oxazol-5(4H)-ones as intermediates in the formation of macrolides, cyclodepsipeptides and cyclopeptides

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEPSIPEPTIDE; CYCLOPEPTIDE; MACROLIDE;

EID: 0033367708     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570360614     Document Type: Conference Paper
Times cited : (18)

References (77)
  • 2
    • 0343757922 scopus 로고    scopus 로고
    • P. Hoet, Ph.D. thesis, Université Catholique de Louvain, 1975
    • P. Hoet, Ph.D. thesis, Université Catholique de Louvain, 1975.
  • 4
    • 0029958424 scopus 로고    scopus 로고
    • C. B. Bucher, A. Linden and H. Heimgartner, Helv. Chim. Acta, 78, 935 (1995); C. B. Bucher and H. Heimgartner, Helv. Chim. Acta, 79, 1903 (1996).
    • (1996) Helv. Chim. Acta , vol.79 , pp. 1903
    • Bucher, C.B.1    Heimgartner, H.2
  • 8
    • 0033597275 scopus 로고    scopus 로고
    • J. Lehmann, A. Linden and H. Heimgartner, Tetrahedron, 54, 8721 (1998); Tetrahedron, 55, 5359 (1999); Helv. Chim. Acta, 82, 888 (1999).
    • (1999) Tetrahedron , vol.55 , pp. 5359
  • 9
    • 0033064044 scopus 로고    scopus 로고
    • J. Lehmann, A. Linden and H. Heimgartner, Tetrahedron, 54, 8721 (1998); Tetrahedron, 55, 5359 (1999); Helv. Chim. Acta, 82, 888 (1999).
    • (1999) Helv. Chim. Acta , vol.82 , pp. 888
  • 11
    • 84987470039 scopus 로고
    • P. Wipf and H. Heimgartner, Helv. Chim. Acta, 69, 1153 (1986); Helv. Chim. Acta, 70, 354 (1987).
    • (1987) Helv. Chim. Acta , vol.70 , pp. 354
  • 13
    • 0000547157 scopus 로고
    • C. Galli, G. Giovanelli, G. Illuminati and L. Mandolini, J. Org. Chem., 44, 1258 (1979); D. F. DeTar and N. P. Luthra, J. Am. Chem. Soc., 102, 4505 (1980); J.-W. Drijfhout, A. Wagenaar and J. B. F. N. Engberts, Tetrahedron Letters, 27, 2423 (1986).
    • (1979) J. Org. Chem. , vol.44 , pp. 1258
    • Galli, C.1    Giovanelli, G.2    Illuminati, G.3    Mandolini, L.4
  • 14
    • 0010473867 scopus 로고
    • C. Galli, G. Giovanelli, G. Illuminati and L. Mandolini, J. Org. Chem., 44, 1258 (1979); D. F. DeTar and N. P. Luthra, J. Am. Chem. Soc., 102, 4505 (1980); J.-W. Drijfhout, A. Wagenaar and J. B. F. N. Engberts, Tetrahedron Letters, 27, 2423 (1986).
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 4505
    • DeTar, D.F.1    Luthra, N.P.2
  • 15
    • 0022615504 scopus 로고
    • C. Galli, G. Giovanelli, G. Illuminati and L. Mandolini, J. Org. Chem., 44, 1258 (1979); D. F. DeTar and N. P. Luthra, J. Am. Chem. Soc., 102, 4505 (1980); J.-W. Drijfhout, A. Wagenaar and J. B. F. N. Engberts, Tetrahedron Letters, 27, 2423 (1986).
    • (1986) Tetrahedron Letters , vol.27 , pp. 2423
    • Drijfhout, J.-W.1    Wagenaar, A.2    Engberts, J.B.F.N.3
  • 18
    • 0343757914 scopus 로고
    • H. T. Clarke, J. R. Johnson and R. Robinson, eds, Princeton University Press
    • J. W. Comforth, The Chemistry of Penicillins, H. T. Clarke, J. R. Johnson and R. Robinson, eds, Princeton University Press, 1949, p 1410.
    • (1949) The Chemistry of Penicillins , pp. 1410
    • Comforth, J.W.1
  • 19
    • 0000549262 scopus 로고
    • R. C. Elderfield, ed, J. Wiley & Sons, New York
    • J. W. Cornforth, Heterocyclic Compounds, Vol. 5, R. C. Elderfield, ed, J. Wiley & Sons, New York, 1957, p 298.
    • (1957) Heterocyclic Compounds , vol.5 , pp. 298
    • Cornforth, J.W.1
  • 31
    • 0343757913 scopus 로고
    • Peptides 1992
    • C. H. Schneider and A. N. Eberle, eds, Leiden
    • M. Rothe, K. Reichert and M. Rosenbauer, Peptides 1992, C. H. Schneider and A. N. Eberle, eds, ESCOM, Leiden, 1993, p 391.
    • (1993) ESCOM , pp. 391
    • Rothe, M.1    Reichert, K.2    Rosenbauer, M.3
  • 33
    • 0342452593 scopus 로고
    • R. C. Sheppard, Experientia, 19, 125 (1963); R. K. A. Giger, H. R. Loosli, M. D. Walkinshaw, B. J. Clark and J. M. Vigouret, Experientia, 43, 1125 (1987).
    • (1963) Experientia , vol.19 , pp. 125
    • Sheppard, R.C.1
  • 36
    • 0026719242 scopus 로고
    • K. Hamano, M. Kinoshita, K. Furuya, M. Miyamoto, Y. Takamatsu, A. Hemmi and K. Tanzawa, J. Antibiot., 45, 899 (1992); M. T. Reese, N. K. Gulavita, Y. Nakao, M. T. Hamann, W. Y. Yoshida, S. J. Coval and P. J. Scheurer, J. Am. Chem. Soc., 118, 11081 (1996); M. Murakami, S. Kodani, K. Ishida, H. Matsuda and K. Yamaguchi, Tetrahedron Letters, 38, 3035 (1997); G. N. Belofsky, P. R. Jensen and W. Fenical, Tetrahedron Letters, 40, 2913 (1999).
    • (1992) J. Antibiot. , vol.45 , pp. 899
    • Hamano, K.1    Kinoshita, M.2    Furuya, K.3    Miyamoto, M.4    Takamatsu, Y.5    Hemmi, A.6    Tanzawa, K.7
  • 37
    • 0029860844 scopus 로고    scopus 로고
    • K. Hamano, M. Kinoshita, K. Furuya, M. Miyamoto, Y. Takamatsu, A. Hemmi and K. Tanzawa, J. Antibiot., 45, 899 (1992); M. T. Reese, N. K. Gulavita, Y. Nakao, M. T. Hamann, W. Y. Yoshida, S. J. Coval and P. J. Scheurer, J. Am. Chem. Soc., 118, 11081 (1996); M. Murakami, S. Kodani, K. Ishida, H. Matsuda and K. Yamaguchi, Tetrahedron Letters, 38, 3035 (1997); G. N. Belofsky, P. R. Jensen and W. Fenical, Tetrahedron Letters, 40, 2913 (1999).
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11081
    • Reese, M.T.1    Gulavita, N.K.2    Nakao, Y.3    Hamann, M.T.4    Yoshida, W.Y.5    Coval, S.J.6    Scheurer, P.J.7
  • 38
    • 0030933127 scopus 로고    scopus 로고
    • K. Hamano, M. Kinoshita, K. Furuya, M. Miyamoto, Y. Takamatsu, A. Hemmi and K. Tanzawa, J. Antibiot., 45, 899 (1992); M. T. Reese, N. K. Gulavita, Y. Nakao, M. T. Hamann, W. Y. Yoshida, S. J. Coval and P. J. Scheurer, J. Am. Chem. Soc., 118, 11081 (1996); M. Murakami, S. Kodani, K. Ishida, H. Matsuda and K. Yamaguchi, Tetrahedron Letters, 38, 3035 (1997); G. N. Belofsky, P. R. Jensen and W. Fenical, Tetrahedron Letters, 40, 2913 (1999).
    • (1997) Tetrahedron Letters , vol.38 , pp. 3035
    • Murakami, M.1    Kodani, S.2    Ishida, K.3    Matsuda, H.4    Yamaguchi, K.5
  • 39
    • 0033538036 scopus 로고    scopus 로고
    • K. Hamano, M. Kinoshita, K. Furuya, M. Miyamoto, Y. Takamatsu, A. Hemmi and K. Tanzawa, J. Antibiot., 45, 899 (1992); M. T. Reese, N. K. Gulavita, Y. Nakao, M. T. Hamann, W. Y. Yoshida, S. J. Coval and P. J. Scheurer, J. Am. Chem. Soc., 118, 11081 (1996); M. Murakami, S. Kodani, K. Ishida, H. Matsuda and K. Yamaguchi, Tetrahedron Letters, 38, 3035 (1997); G. N. Belofsky, P. R. Jensen and W. Fenical, Tetrahedron Letters, 40, 2913 (1999).
    • (1999) Tetrahedron Letters , vol.40 , pp. 2913
    • Belofsky, G.N.1    Jensen, P.R.2    Fenical, W.3
  • 40
    • 0342452592 scopus 로고    scopus 로고
    • K. N. Koch, planned Ph.D. thesis, University of Zürich
    • K. N. Koch, planned Ph.D. thesis, University of Zürich.
  • 45
    • 0016270242 scopus 로고
    • Y. A. Ovchinnikov, FEBS Letters, 44, 1 (1974); G. N. Tishchenko, Molecular Structure and Biological Activity, J. F. Griffin and W. L. Duax, eds, Elsevier Science Publishers, Amsterdam, 1982, p 229; G. N. Tishchenko, Z. Karimov, B. K. Vainshtein, A. V. Evstratov, V. T. Ivanov and Y. A. Ovchinnikov, FEBS Letters, 65, 315 (1976).
    • (1974) FEBS Letters , vol.44 , pp. 1
    • Ovchinnikov, Y.A.1
  • 46
    • 0016270242 scopus 로고
    • J. F. Griffin and W. L. Duax, eds, Elsevier Science Publishers, Amsterdam
    • Y. A. Ovchinnikov, FEBS Letters, 44, 1 (1974); G. N. Tishchenko, Molecular Structure and Biological Activity, J. F. Griffin and W. L. Duax, eds, Elsevier Science Publishers, Amsterdam, 1982, p 229; G. N. Tishchenko, Z. Karimov, B. K. Vainshtein, A. V. Evstratov, V. T. Ivanov and Y. A. Ovchinnikov, FEBS Letters, 65, 315 (1976).
    • (1982) Molecular Structure and Biological Activity , pp. 229
    • Tishchenko, G.N.1
  • 49
    • 0342452588 scopus 로고    scopus 로고
    • J. E. F. Magirius, Ph.D. thesis, University of Zurich, 1995; J. E. F. Magirius, A. Linden and H. Heimgartner, in preparation
    • J. E. F. Magirius, Ph.D. thesis, University of Zurich, 1995; J. E. F. Magirius, A. Linden and H. Heimgartner, in preparation.
  • 52
    • 0038991855 scopus 로고
    • D. H. Hey, ed, Butterworth, London
    • T. Wieland and C. Birr, International Review of Science, Organic Chemistry, Vol. 6, D. H. Hey, ed, Butterworth, London, 1976, p 183; G. Schmidt, Topics Curr. Chem., 136, 109 (1986); U. Schmidt, Nachr. Chem. Techn. Lab., 37, 1034 (1989); H. A. Nagarajaram and C. Ramakrishnan, J. Biosci., 20, 591 (1995).
    • (1976) International Review of Science, Organic Chemistry , vol.6 , pp. 183
    • Wieland, T.1    Birr, C.2
  • 53
    • 0000460445 scopus 로고
    • T. Wieland and C. Birr, International Review of Science, Organic Chemistry, Vol. 6, D. H. Hey, ed, Butterworth, London, 1976, p 183; G. Schmidt, Topics Curr. Chem., 136, 109 (1986); U. Schmidt, Nachr. Chem. Techn. Lab., 37, 1034 (1989); H. A. Nagarajaram and C. Ramakrishnan, J. Biosci., 20, 591 (1995).
    • (1986) Topics Curr. Chem. , vol.136 , pp. 109
    • Schmidt, G.1
  • 54
    • 0001143188 scopus 로고
    • T. Wieland and C. Birr, International Review of Science, Organic Chemistry, Vol. 6, D. H. Hey, ed, Butterworth, London, 1976, p 183; G. Schmidt, Topics Curr. Chem., 136, 109 (1986); U. Schmidt, Nachr. Chem. Techn. Lab., 37, 1034 (1989); H. A. Nagarajaram and C. Ramakrishnan, J. Biosci., 20, 591 (1995).
    • (1989) Nachr. Chem. Techn. Lab. , vol.37 , pp. 1034
    • Schmidt, U.1
  • 55
    • 51249162754 scopus 로고
    • T. Wieland and C. Birr, International Review of Science, Organic Chemistry, Vol. 6, D. H. Hey, ed, Butterworth, London, 1976, p 183; G. Schmidt, Topics Curr. Chem., 136, 109 (1986); U. Schmidt, Nachr. Chem. Techn. Lab., 37, 1034 (1989); H. A. Nagarajaram and C. Ramakrishnan, J. Biosci., 20, 591 (1995).
    • (1995) J. Biosci. , vol.20 , pp. 591
    • Nagarajaram, H.A.1    Ramakrishnan, C.2
  • 57
    • 0002891433 scopus 로고
    • Peptides 1990
    • I. Dannecker-Dörig, Ph.D. thesis, University of Zürich, 1995, E. Giralt and D. Andreu, eds, Leiden
    • I. Dannecker-Dörig, Ph.D. thesis, University of Zürich, 1995; I. Dannecker-Dörig and H. Heimgartner, Peptides 1990, E. Giralt and D. Andreu, eds, ESCOM, Leiden, 1991, p 460.
    • (1991) ESCOM , pp. 460
    • Dannecker-Dörig, I.1    Heimgartner, H.2
  • 58
    • 0343757697 scopus 로고    scopus 로고
    • F. S. Arnhold, Ph.D. thesis, University of Zürich, 1997
    • F. S. Arnhold, Ph.D. thesis, University of Zürich, 1997.
  • 59
    • 0343321922 scopus 로고    scopus 로고
    • F. S. Arnhold and H. Heimgartner, unpublished results
    • F. S. Arnhold and H. Heimgartner, unpublished results.
  • 61
    • 0006913662 scopus 로고
    • W. Steglich and G. Höfle, Chem. Ber., 102, 883 (1969); Chem. Ber., 102, 1129 (1969); Chem. Ber., 104, 3644 (1971); G. Höfle and W. Steglich, Chem. Ber., 104, 1408 (1971).
    • (1969) Chem. Ber. , vol.102 , pp. 883
    • Steglich, W.1    Höfle, G.2
  • 62
    • 84980915455 scopus 로고
    • W. Steglich and G. Höfle, Chem. Ber., 102, 883 (1969); Chem. Ber., 102, 1129 (1969); Chem. Ber., 104, 3644 (1971); G. Höfle and W. Steglich, Chem. Ber., 104, 1408 (1971).
    • (1969) Chem. Ber. , vol.102 , pp. 1129
  • 63
    • 0343321914 scopus 로고
    • W. Steglich and G. Höfle, Chem. Ber., 102, 883 (1969); Chem. Ber., 102, 1129 (1969); Chem. Ber., 104, 3644 (1971); G. Höfle and W. Steglich, Chem. Ber., 104, 1408 (1971).
    • (1971) Chem. Ber. , vol.104 , pp. 3644
  • 64
    • 84943836656 scopus 로고
    • W. Steglich and G. Höfle, Chem. Ber., 102, 883 (1969); Chem. Ber., 102, 1129 (1969); Chem. Ber., 104, 3644 (1971); G. Höfle and W. Steglich, Chem. Ber., 104, 1408 (1971).
    • (1971) Chem. Ber. , vol.104 , pp. 1408
    • Höfle, G.1    Steglich, W.2
  • 66
    • 0343321915 scopus 로고    scopus 로고
    • S. P. Fritschi, Ph.D. thesis, University of Zurich, 1995
    • S. P. Fritschi, Ph.D. thesis, University of Zurich, 1995.
  • 67
    • 84982056674 scopus 로고
    • S. Götze, B. Kübel and W. Steglich, Chem. Ber., 109, 2331 (1976); B. Kübel, P. Gruber, R. Hurnaus and W. Steglich, Chem. Ber., 112, 128 (1979); R. Lohmar and W. Steglich, Chem. Ber., 113, 3706 (1980); H. Wegmann, G. Schulz and W. Steglich, Chem. Ber., 113, 1736 (1980); H. Wegmann and W. Steglich, Chem. Ber., 114, 2580 (1981).
    • (1976) Chem. Ber. , vol.109 , pp. 2331
    • Götze, S.1    Kübel, B.2    Steglich, W.3
  • 68
    • 0001196145 scopus 로고
    • S. Götze, B. Kübel and W. Steglich, Chem. Ber., 109, 2331 (1976); B. Kübel, P. Gruber, R. Hurnaus and W. Steglich, Chem. Ber., 112, 128 (1979); R. Lohmar and W. Steglich, Chem. Ber., 113, 3706 (1980); H. Wegmann, G. Schulz and W. Steglich, Chem. Ber., 113, 1736 (1980); H. Wegmann and W. Steglich, Chem. Ber., 114, 2580 (1981).
    • (1979) Chem. Ber. , vol.112 , pp. 128
    • Kübel, B.1    Gruber, P.2    Hurnaus, R.3    Steglich, W.4
  • 69
    • 84982058251 scopus 로고
    • S. Götze, B. Kübel and W. Steglich, Chem. Ber., 109, 2331 (1976); B. Kübel, P. Gruber, R. Hurnaus and W. Steglich, Chem. Ber., 112, 128 (1979); R. Lohmar and W. Steglich, Chem. Ber., 113, 3706 (1980); H. Wegmann, G. Schulz and W. Steglich, Chem. Ber., 113, 1736 (1980); H. Wegmann and W. Steglich, Chem. Ber., 114, 2580 (1981).
    • (1980) Chem. Ber. , vol.113 , pp. 3706
    • Lohmar, R.1    Steglich, W.2
  • 70
    • 84982056674 scopus 로고
    • S. Götze, B. Kübel and W. Steglich, Chem. Ber., 109, 2331 (1976); B. Kübel, P. Gruber, R. Hurnaus and W. Steglich, Chem. Ber., 112, 128 (1979); R. Lohmar and W. Steglich, Chem. Ber., 113, 3706 (1980); H. Wegmann, G. Schulz and W. Steglich, Chem. Ber., 113, 1736 (1980); H. Wegmann and W. Steglich, Chem. Ber., 114, 2580 (1981).
    • (1980) Chem. Ber. , vol.113 , pp. 1736
    • Wegmann, H.1    Schulz, G.2    Steglich, W.3
  • 71
    • 84982078049 scopus 로고
    • S. Götze, B. Kübel and W. Steglich, Chem. Ber., 109, 2331 (1976); B. Kübel, P. Gruber, R. Hurnaus and W. Steglich, Chem. Ber., 112, 128 (1979); R. Lohmar and W. Steglich, Chem. Ber., 113, 3706 (1980); H. Wegmann, G. Schulz and W. Steglich, Chem. Ber., 113, 1736 (1980); H. Wegmann and W. Steglich, Chem. Ber., 114, 2580 (1981).
    • (1981) Chem. Ber. , vol.114 , pp. 2580
    • Wegmann, H.1    Steglich, W.2
  • 73
    • 0342452374 scopus 로고
    • D. Obrecht and H. Heimgartner, Tetrahedron Letters, 25, 1712 (1984); D. Obrecht, U. Bohdal, R. Ruffieux and K. Müller, Helv. Chim. Acta, 77, 1423 (1994).
    • (1984) Tetrahedron Letters , vol.25 , pp. 1712
    • Obrecht, D.1    Heimgartner, H.2
  • 75
    • 0343177218 scopus 로고
    • H. Staudinger and J. Meyer, Helv. Chim. Acta, 2, 635 (1919); S. Nagarajan and B. Ganem, J. Org. Chem., 52, 5044 (1987); N. Knouzi, M. Vaultier and R. Carrié, Bull. Soc. Chim. France, 815 (1985).
    • (1919) Helv. Chim. Acta , vol.2 , pp. 635
    • Staudinger, H.1    Meyer, J.2
  • 76
    • 0023577508 scopus 로고
    • H. Staudinger and J. Meyer, Helv. Chim. Acta, 2, 635 (1919); S. Nagarajan and B. Ganem, J. Org. Chem., 52, 5044 (1987); N. Knouzi, M. Vaultier and R. Carrié, Bull. Soc. Chim. France, 815 (1985).
    • (1987) J. Org. Chem. , vol.52 , pp. 5044
    • Nagarajan, S.1    Ganem, B.2
  • 77


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.