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84988764094
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note
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Kende has reported a synthetic intermediate having a related structure in his approach to Punctaporonin B. See ref. 8a.
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4
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For reviews on the use of samarium(II) iodide in organic synthesis: (a) J. A. Soderquist, Aldrichimica Acta, 1991, 24, 15
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(b) D. Johnston, C. F. McCusker, K. Muir and D. J. Procter, J. Chem. Soc., Perkin Trans. 1, 2000, 681.
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Prior to our work, a single example of such a cyclisation had been described by Weinges: K. Weinges, S. B. Schmidbauer and H. Schick, Chem. Ber., 1994, 127, 1305.
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For a preliminary account of this work, see: D. Johnston, N. Francon, D. J. Edmonds and D. J. Procter, Org. Lett., 2001, 2001.
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84988751645
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note
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Commercially available 'anhydrous' ytterbium triflate was dried thoroughly before use (140 °C/0.1 mmHg/20 h).
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(a) G. A. Molander, E. R. Burkhardt and P. Weinig, J. Org. Chem., 1990, 55, 4990
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(b) Molander has recently described a similar diastereoselective, sequential addition/lactonisation process triggered by the addition of an organoytterbium to a functionalised cyclopentanone, a cyclohexanone; G. A. Molander and C. Köllner, J. Org. Chem., 2000, 65, 8333.
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24
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