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For a review of the reactions of trialkylsilyloxy furans with electrophiles, see: (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607. For related reactions, see: (b) Harding, K. E.; Coleman, M. T.; Liu, L. T. Tetrahedron Lett. 1991, 31, 3795. Morimoto, Y.; Nishida, K.; Hayashi, Y. Tetrahedron Lett. 1993, 34, 5773. Pelter, A.; Ward, R. S.; Sirit, A. Tetrahedron: Asymmetry 1994, 5, 1745. (e) Hanessian, S.; Raghavan, S. Biorg. Med. Chem. Lett. 1994, 4, 1697. (f) Pichon, M.; Figadére, B.; Cavé, A. Tetrahedron Lett. 1996, 37, 7963.
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Pichon, M.1
Figadére, B.2
Cavé, A.3
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42
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13044251213
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note
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1H NMR spectroscopy; the structures of compounds 11b-g, 14c, 18, 19, 24, and 26 were determined by X-ray crystallography.
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43
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37049081005
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(a) Brimbie, M. A.; Brimble, M. T.; Gibson, J. J. J. Chem. Soc., Perkin Trans. 1 1989, 179.
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J. Chem. Soc., Perkin Trans. 1
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Brimbie, M.A.1
Brimble, M.T.2
Gibson, J.J.3
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44
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0024992412
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(b) Jefford, C. W.; Sledeski, A. W.; Rossier, J.-C.; Boukouvalas, J. Tetrahedron Lett. 1990, 31, 5741.
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Tetrahedron Lett.
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Jefford, C.W.1
Sledeski, A.W.2
Rossier, J.-C.3
Boukouvalas, J.4
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46
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0000764418
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Nagasaka, T.; Tamano, H.; Hamaguchi, F. Heterocycles 1986, 24, 1231.
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Heterocycles
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Nagasaka, T.1
Tamano, H.2
Hamaguchi, F.3
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48
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0001053043
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Shono, T.; Matsumura, Y.; Tsubatya, K.; Sugihara, Y.; Shin-ichiro, Y.; Kanazawa, T.; Aoki, T. J. Am. Chem. Soc. 1982, 104, 6697. See also ref 8e.
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Shono, T.1
Matsumura, Y.2
Tsubatya, K.3
Sugihara, Y.4
Shin-ichiro, Y.5
Kanazawa, T.6
Aoki, T.7
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49
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13044284119
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note
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Numbering of all intermediates corresponds to the numbering scheme shown for croomine (1).
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51
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0000444884
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(a) Dean, R. T.; Padgett, H. C.; Rapoport, H. J. Am. Chem. Soc. 1976, 98, 7448.
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Dean, R.T.1
Padgett, H.C.2
Rapoport, H.3
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53
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0000630624
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(c) Johansen, J. E.; Christie, B. D.; Rapoport, H. J. Org. Chem. 1981, 46, 4914.
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Johansen, J.E.1
Christie, B.D.2
Rapoport, H.3
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54
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0345313263
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For example, see: (a) Wasserman, H.; Tremper, A. W. Tetrahedron Lett. 1977, 1449. (b) van Tamelen, E. E.; Haarstead, V. B.; Orvis, R. L. Tetrahedron 1967, 24, 687. van Tamelen, E. E.; Oliver, L. K. J. Am. Chem. Soc. 1970, 92, 2136; Bioorg. Chem. 1976, 5, 309.
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Tetrahedron Lett.
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Wasserman, H.1
Tremper, A.W.2
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55
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0014232480
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For example, see: (a) Wasserman, H.; Tremper, A. W. Tetrahedron Lett. 1977, 1449. (b) van Tamelen, E. E.; Haarstead, V. B.; Orvis, R. L. Tetrahedron 1967, 24, 687. van Tamelen, E. E.; Oliver, L. K. J. Am. Chem. Soc. 1970, 92, 2136; Bioorg. Chem. 1976, 5, 309.
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Tetrahedron
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Van Tamelen, E.E.1
Haarstead, V.B.2
Orvis, R.L.3
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56
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0000127055
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For example, see: (a) Wasserman, H.; Tremper, A. W. Tetrahedron Lett. 1977, 1449. (b) van Tamelen, E. E.; Haarstead, V. B.; Orvis, R. L. Tetrahedron 1967, 24, 687. van Tamelen, E. E.; Oliver, L. K. J. Am. Chem. Soc. 1970, 92, 2136; Bioorg. Chem. 1976, 5, 309.
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Van Tamelen, E.E.1
Oliver, L.K.2
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57
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0017165780
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For example, see: (a) Wasserman, H.; Tremper, A. W. Tetrahedron Lett. 1977, 1449. (b) van Tamelen, E. E.; Haarstead, V. B.; Orvis, R. L. Tetrahedron 1967, 24, 687. van Tamelen, E. E.; Oliver, L. K. J. Am. Chem. Soc. 1970, 92, 2136; Bioorg. Chem. 1976, 5, 309.
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Bioorg. Chem.
, vol.5
, pp. 309
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58
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13044282425
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note
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Approximately 5% of another stereoisomer that was not identified was also isolated.
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-
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59
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84986437005
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As implemented by MacroModel v6.0, available from Columbia University. See: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. J. Comput. Chem. 1990, 11, 440.
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Mohamadi, F.1
Richards, N.G.J.2
Guida, W.C.3
Liskamp, R.4
Lipton, M.5
Caufield, C.6
Chang, G.7
Hendrickson, T.8
Still, W.9
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60
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13044258399
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note
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As implemented by CONFORT v2 from Dr. Robert Pearlman at the University of Texas at Austin.
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