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0011953242
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This work was carried out at Hokkaido University
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1. This work was carried out at Hokkaido University.
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2
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2. Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Goto, T.; Hashimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 109, 5031-5033.
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3. For the total syntheses of FK 506 1, see: (a) Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998-3017.
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(c) Jones, A. B.; Villalobos, A.; Linde II, R. G.; Danishefsky, S. J. J. Org. Chem. 1990, 55, 2786-2797.
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7
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For the synthetic approaches toward FK 506 1, see: (e) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643-4644.
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(i) Wasserman, H. H.; Rotello, V. M.; Williams, D. R.; Benbow, J. W. J. Org. Chem. 1989, 54, 2785-2786.
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(l) Smith III, A. B.; Hale, K. J.; Laakso, L. M.; Chen, K.; Riera, A. ibid. 1989, 30, 6963-6966.
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(n) Kocienski, P.; Stocks, M.; Donald, D.; Perry, M. Synlett 1990, 38-39.
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(o) Rao, A. V. R.; Chakraborty, T. K.; Reddy, K. L. Tetrahedron Lett. 1990, 31, 1439-1442.
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(p) Rao, A. V. R.; Chakraborty, T. K.; Purandare, A. V. ibid. 1990, 31, 1443-1446.
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(q) Stocks, M.; Kocienski, P.; Donald, D. K. ibid. 1990, 31, 1637-1640.
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(r) Ireland, R. E.; Wipf, P.; Roper, T. D. J. Org. Chem. 1990, 55, 2284-2285.
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31
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0011961246
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note
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13C NMR spectrum.
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35
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33845553211
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Table of conformational energies-1967
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Allinger, N. L.; Eliel, E. L. Eds.; John Wiley & Sons, Inc.: New York
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17. Hirsch, J. A. Table of Conformational Energies-1967. In Topics in Stereochemistry; Allinger, N. L.; Eliel, E. L. Eds.; John Wiley & Sons, Inc.: New York, 1967; Vol. 1, pp. 199-222.
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0001274745
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19. For metal ion controlled addition to α,β-dialkoxy carbonyl compounds related to our substrate 26, see: Mead, K.; Macdonald, T. L. J. Org. Chem. 1985, 50, 422-424.
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20. For a review on chelation or non-chelation control in addition reactions of chiral α-and β-alkoxy carbonyl compounds, see: Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556-569.
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23. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
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