메뉴 건너뛰기




Volumn 4, Issue , 2007, Pages 263-351

The Total Synthesis of Ionophores

Author keywords

Boromycin; Gramacidins; Polyether antibiotics; Siderophores; Synthetic analogs

Indexed keywords

SPEECH SYNTHESIS;

EID: 85050057786     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470129678.ch3     Document Type: Chapter
Times cited : (39)

References (284)
  • 4
    • 84918049163 scopus 로고
    • Yu. A. Ovchinnikov and M. N. Kolosov, Eds., Elsevier/North Holland Biomedical Press
    • Yu. A. Ovchinnikov, Frontiers in Bioorganic Chemistry and Molecular Biology, Yu. A. Ovchinnikov and M. N. Kolosov, Eds., Elsevier/North Holland Biomedical Press, 1979, pp. 129-165.
    • (1979) Frontiers in Bioorganic Chemistry and Molecular Biology , pp. 129-165
    • Ovchinnikov, Y.A.1
  • 21
    • 15244340021 scopus 로고
    • B. A. Callingham, Ed., University Park Press, Baltimore, Md
    • A. Finkelstein, Drugs and Transport Processes, B. A. Callingham, Ed., University Park Press, Baltimore, Md., 1973, pp. 241-250.
    • (1973) Drugs and Transport Processes , pp. 241-250
    • Finkelstein, A.1
  • 22
    • 33749393584 scopus 로고
    • J. ApSimon, Ed, Wiley-Interscience, New York
    • F. Johnson, The Total Synthesis of Natural Products, Vol. 1, J. ApSimon, Ed., pp. 331-466, Wiley-Interscience, New York, 1973.
    • (1973) The Total Synthesis of Natural Products , vol.1 , pp. 331-466
    • Johnson, F.1
  • 30
    • 85080381717 scopus 로고    scopus 로고
    • see footnote 28 of 26(a)
    • see footnote 28 of 26(a).
  • 32
    • 84910185839 scopus 로고
    • B. A. Callingham, Ed., University Park Press, Baltimore, Md, (and references cited therein)
    • L. G. M. Gordon, Drugs and Transport Processes, B. A. Callingham, Ed., University Park Press, Baltimore, Md., 1973, pp. 251-264 (and references cited therein).
    • (1973) Drugs and Transport Processes , pp. 251-264
    • Gordon, L.G.M.1
  • 37
    • 85080381205 scopus 로고    scopus 로고
    • Private communication from K. L. Rinehart; see also footnotes 18b and 28 of Ref. 26(a)
    • Private communication from K. L. Rinehart; see also footnotes 18b and 28 of Ref. 26(a).
  • 42
    • 85080349893 scopus 로고
    • Yu. A. Ovchinnikov, V. T. Ivanov, A. Miroshnikov, K. Khaliluline, and N. N. Uvarova
    • See, for example
    • See, for example, Yu. A. Ovchinnikov, V. T. Ivanov, A. Miroshnikov, K. Khaliluline, and N. N. Uvarova, Khim. Prir. Soedin (USSR), 469, (1971)
    • (1971) Khim. Prir. Soedin (USSR) , pp. 469
  • 52
    • 84917982028 scopus 로고
    • Chapter 10, in MTP Int. Rev. of Science, Biochemistry Series, Butterworth, London
    • W. Epstein, Membrane Transport, Chapter 10, in MTP Int. Rev. of Science, Biochemistry Series, Vol. 2, Butterworth, London, (1975).
    • (1975) Membrane Transport , vol.2
    • Epstein, W.1
  • 72
    • 85080398741 scopus 로고
    • Academic Press, New York
    • G. R. Pettit, Synthetic Peptides, Vol. 3, p. 385, Academic Press, New York, 1975.
    • (1975) Synthetic Peptides , vol.3 , pp. 385
    • Pettit, G.R.1
  • 86
    • 0003868249 scopus 로고
    • Iron and Its Role in Microbial Physiology
    • J. B. Neiland, Ed., Chap. 1, Academic Press, New York
    • J. B. Neilands, "Iron and Its Role in Microbial Physiology", in Microbial Iron Metabolism, J. B. Neiland, Ed., Chap. 1, Academic Press, New York, 1974;
    • (1974) Microbial Iron Metabolism
    • Neilands, J.B.1
  • 87
    • 84867998616 scopus 로고
    • Iron Transport in Gram-Positive and Acid-Fast Bacilli
    • Chap. 4, Academic Press, New York
    • B. R. Byers, "Iron Transport in Gram-Positive and Acid-Fast Bacilli", Chap. 4, Academic Press, New York, 1974;
    • (1974)
    • Byers, B.R.1
  • 88
    • 0343294606 scopus 로고
    • Biosynthesis and Mechanism of Action of Hydroxamate-Type Sidero-chromes
    • Chap. 5, Academic Press, New York
    • T. Emery, "Biosynthesis and Mechanism of Action of Hydroxamate-Type Sidero-chromes", Chap. 5, Academic Press, New York, 1974;
    • (1974)
    • Emery, T.1
  • 89
    • 0344868325 scopus 로고
    • Iron Transport in the Enteric Bacteria
    • Chap. 3, Academic Press, New York
    • H. Rosenberg and I. G. Young, "Iron Transport in the Enteric Bacteria", Chap. 3, Academic Press, New York, 1974.
    • (1974)
    • Rosenberg, H.1    Young, I.G.2
  • 104
  • 141
    • 85080428863 scopus 로고    scopus 로고
    • 2 neat at reflux for 3 hr)
    • 2 neat at reflux for 3 hr).
  • 142
    • 85080361919 scopus 로고    scopus 로고
    • See the accompanying chapter on Macrocyclic Synthesis by R. K. Boeckman for further details and examples
    • See the accompanying chapter on Macrocyclic Synthesis by R. K. Boeckman for further details and examples.
  • 160
    • 0009347902 scopus 로고
    • Personal communication from D. J. Cram. See also
    • Personal communication from D. J. Cram. See also J. G. DeVries and R. M. Kellogg, J. Am. Chem. Soc., 101, 2759 (1979).
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 2759
    • DeVries, J.G.1    Kellogg, R.M.2
  • 164
  • 165
    • 0010307479 scopus 로고
    • See for example
    • See for example V. Prelog, Pure Appl. Chem., 50, 893 (1978);
    • (1978) Pure Appl. Chem. , vol.50 , pp. 893
    • Prelog, V.1
  • 168
    • 84937193113 scopus 로고
    • Accf. Chem. Res., 11, 49 (1978)
    • J. M. Lehn, Pure Appl. Chem., 49, 857 (1977); Accf. Chem. Res., 11, 49 (1978).
    • (1977) Pure Appl. Chem. , vol.49 , pp. 857
    • Lehn, J.M.1
  • 175
    • 85080397026 scopus 로고
    • See also
    • See also N. Otake et al., J. Antibiot., 30, 186 (1972).
    • (1972) J. Antibiot. , vol.30 , pp. 186
    • Otake, N.1
  • 192
    • 84970553078 scopus 로고
    • for mechanistic details and also, for further details on this chemistry of preparing tetrahydrofurans
    • for mechanistic details and also T. Fukarama, B. Vranesic, D. P. Negri, and Y. Kishi, Tetrahedron Lett., 2741 (1978) for further details on this chemistry of preparing tetrahydrofurans.
    • (1978) Tetrahedron Lett. , pp. 2741
    • Fukarama, T.1    Vranesic, B.2    Negri, D.P.3    Kishi, Y.4
  • 223
    • 16044365644 scopus 로고
    • J. W. Corcoran and F. E. Hahn, Eds., Springer-Verlag, Heidelberg
    • W. Pache, Boromycin, in Antibiotics, Vol. 3, J. W. Corcoran and F. E. Hahn, Eds., Springer-Verlag, Heidelberg, 1975, p. 585.
    • (1975) Antibiotics , vol.3 , pp. 585
    • Pache, W.1    Boromycin2
  • 224
    • 85080313916 scopus 로고
    • Seminar at the Upjohn Company, June 12, 1979 and private communication by J. D. White, Oregon State Univ. (collaborators are O. Dhingra and B. Sheldon); 179th ACS National Meeting
    • Seminar at the Upjohn Company, June 12, 1979 and private communication by J. D. White, Oregon State Univ. (collaborators are O. Dhingra and B. Sheldon); 179th ACS National Meeting, Abstr. ORGN 48, 1980.
    • (1980) Abstr. ORGN , pp. 48
  • 229
    • 85080361883 scopus 로고    scopus 로고
    • 4
    • 4
  • 235
    • 0010858507 scopus 로고
    • 1108, and references cited therein to earlier communications;
    • W. Rashofer, G. Oepen, and F. Vögtle, Chem. Ber., 111, 419, 1108 (1978) and references cited therein to earlier communications;
    • (1978) Chem. Ber. , vol.111 , pp. 419
    • Rashofer, W.1    Oepen, G.2    Vögtle, F.3
  • 242
    • 85080439246 scopus 로고
    • Antibiotics that Affect Membrane Permeability
    • Oxford University Press, Chap. 6
    • W. B. Pratt, "Antibiotics that Affect Membrane Permeability," in Fundamentals of Chemotherapy, Oxford University Press, 1973, Chap. 6.
    • (1973) Fundamentals of Chemotherapy
    • Pratt, W.B.1
  • 246
    • 85080432336 scopus 로고
    • unpublished results, The Upjohn Co, See also Refs. 206 and 214
    • R. J. Seely, unpublished results, The Upjohn Co., 1975. See also Refs. 206 and 214.
    • (1975)
    • Seely, R.J.1
  • 257
    • 85050048842 scopus 로고
    • [See full account in J. Org. Chem., 38, 2489 (1973)]
    • W. L. Parker, J. Am. Chem. Soc., 91, 7208 (1969). [See full account in J. Org. Chem., 38, 2489 (1973)].
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 7208
    • Parker, W.L.1
  • 261
    • 84912721574 scopus 로고
    • L. Ernster, R. W. Estabrook, and E. C. Slater, Eds, Elsevier, Amsterdam
    • E. Carafoli and G. Sottocasa, in Dynamics of Energy-transducing Membranes, L. Ernster, R. W. Estabrook, and E. C. Slater, Eds., 1974, Elsevier, Amsterdam, pp. 455-469.
    • (1974) Dynamics of Energy-transducing Membranes , pp. 455-469
    • Carafoli, E.1    Sottocasa, G.2
  • 268
    • 85080392989 scopus 로고    scopus 로고
    • Private communication from P. A. Grieco, Univ. of Pittsburg (July, 1979);
    • Private communication from P. A. Grieco, Univ. of Pittsburg (July, 1979);
  • 270
    • 0018675370 scopus 로고
    • The diastereoisomer of 14 was conveniently utilized in a synthesis of methylnolide
    • The diastereoisomer of 14 was conveniently utilized in a synthesis of methylnolide, P. A. Grieco, Y. Ohfune, Y. Yokoyama, and W. Owens, J. Am. Chem. Soc., 101, 4750 (1979);
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 4750
    • Grieco, P.A.1    Ohfune, Y.2    Yokoyama, Y.3    Owens, W.4
  • 274
    • 0002078469 scopus 로고
    • private communication (July, 1979), The synthesis of 10 was just communicated in, and related chemistry described in J. Org. Chem., 45, 48, 197 (1980))
    • R. E. Ireland, S. Thaisrivongs, C. S. Wilcox, and C. G. McGarvey, private communication (July, 1979). (The synthesis of 10 was just communicated in J. Am. Chem. Soc., 102, 1155 (1980) and related chemistry described in J. Org. Chem., 45, 48, 197 (1980)).
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 1155
    • Ireland, R.E.1    Thaisrivongs, S.2    Wilcox, C.S.3    McGarvey, C.G.4
  • 276
    • 49549130554 scopus 로고
    • report that in acetone/water as the solvent combination of choice the diol is normally recovered underivitized
    • V. VanRheenan, R. C. Kelly, and D. Y. Cha, Tetrahedron Lett., 1973 (1976) report that in acetone/water as the solvent combination of choice the diol is normally recovered underivitized.
    • (1976) Tetrahedron Lett. , pp. 1973
    • VanRheenan, V.1    Kelly, R.C.2    Cha, D.Y.3
  • 277
    • 0000588779 scopus 로고    scopus 로고
    • Private communication from W. C. Still, Columbia University (August, 1979, J. McDonald and D. Collum and co-worker; just communicated in J. Am. Chem. Soc., 102, 2117, 2118, 2120 (1980))
    • Private communication from W. C. Still, Columbia University (August, 1979, J. McDonald and D. Collum and co-worker; just communicated in J. Am. Chem. Soc., 102, 2117, 2118, 2120 (1980)).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.