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2, -78°C, 70%) to give nortricyclanone derivative 21 (Aceña, J. L. PhD Thesis, 1996, Universidad Complutense de Madrid. Unpublished results). For related processes, see: (a) Rajapaksa, D.; Keay, B. A.; Rodrigo, R. Can. J. Chem. 1984, 62, 826-827.
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0342475864
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note
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3CN as solvent and further elimination of one of the phenylsulfonyl groups employing t-BuOK in equimolecular amount lead to 2b in high yields (Scheme 10).
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37049075524
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(b) For an enantioselective version of this process, see
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0343345329
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note
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In comparative experiments with those reported by Crandall et al. (see Ref. 8a) and McDonald et al. (see Ref. 12a), we have observed that the unsubstituted bicyclo[2.2.1]hept-2-ene-exo-oxide reacts with LDA in the same conditions used in this work to give nortricyclanol 3a in 88% yield. These conditions should be compared with those reported (reflux, ether-benzene, 50 h).
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44
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0000813335
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(a) Kowalski, C.; Creary, X.; Rollin, A. J.; Burke, M. C. J. Org. Chem. 1978, 43, 2601-2608.
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(b) We thank one of the referees for this observation
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(b) Wittig, G.; Schmidt, H.-J.; Renner, H. Chem. Ber. 1962, 95, 2377. We thank one of the referees for this observation.
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Oxford: Pergamon Press
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Simpkins N.S. Sulfones in Organic Synthesis. Tetrahedron Organic Series. 1993;357 Pergamon Press, Oxford.
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