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73149106260
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The numbering used in this paper refers to the corresponding centers of vinigrol
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The numbering used in this paper refers to the corresponding centers of vinigrol.
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28
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77952559966
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For a review of thermal cyclization of unsaturated ketones see
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73149112929
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Initial attempts to carry out the epoxidation of the intermediate alcohol failed; the resulting epoxide rapidly underwent an intramolecular ring opening by the hydroxyl group producing the corresponding cyclic ether
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Initial attempts to carry out the epoxidation of the intermediate alcohol failed; the resulting epoxide rapidly underwent an intramolecular ring opening by the hydroxyl group producing the corresponding cyclic ether.
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30
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73149111596
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The ratio of 12 and its epimer 13 depends upon the experimental conditions of the hydrogenation and may vary from 2:3 to 2:1. The best result (2:1) was obtained when the reaction mixture was stirred under hydrogen in the presence of a large amount of catalyst for 17 h (see Supporting Information).
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The ratio of 12 and its epimer 13 depends upon the experimental conditions of the hydrogenation and may vary from 2:3 to 2:1. The best result (2:1) was obtained when the reaction mixture was stirred under hydrogen in the presence of a large amount of catalyst for 17 h (see Supporting Information).
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31
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3042662232
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It is known that commercial 10% Pd/C preparations are acidic and exhibit a marked tendency to cleave acid-sensitive alcohols protective groups such as TES or THP ethers. See, for example: Ikawa, T.; Sajiki, H.; Hirota, K. Tetrahedron 2004, 60, 6189.
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It is known that commercial 10% Pd/C preparations are acidic and exhibit a marked tendency to cleave acid-sensitive alcohols protective groups such as TES or THP ethers. See, for example: Ikawa, T.; Sajiki, H.; Hirota, K. Tetrahedron 2004, 60, 6189.
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32
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33847799526
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For example, see: a
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For example, see: (a) Thompson, H. W.; McPherson, E.; Lences, B. L. J. Org. Chem. 1976, 41, 2903.
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73149087766
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Initial attempts to prepare alcohol 14 from by reductive opening of cyclic carbonate 22 or from the corresponding cyclic sulfate were unsuccessful.
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Initial attempts to prepare alcohol 14 from by reductive opening of cyclic carbonate 22 or from the corresponding cyclic sulfate were unsuccessful.
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35
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73149116748
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CCDC 747695, 747694, 747693, 747696, and 747697 (17, 22, 25, 28, and 32, respectively) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge crystallographic Data centre at www.ccdc.com.ac.uk/data/cif.
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CCDC 747695, 747694, 747693, 747696, and 747697 (17, 22, 25, 28, and 32, respectively) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge crystallographic Data centre at www.ccdc.com.ac.uk/data/cif.
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72249103425
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While the manuscript was under revision, Baran and coworkers published the first total synthesis of vinigrol. Maimone, T. J, Shi, J, Ashida, S, Baran, P. S. J. Am. Chem. Soc. ASAP October 30 2009, DOI: 10 1021/ja908194b
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While the manuscript was under revision, Baran and coworkers published the first total synthesis of vinigrol. Maimone, T. J.; Shi, J.; Ashida, S.; Baran, P. S. J. Am. Chem. Soc. ASAP October 30 2009, DOI: 10 1021/ja908194b.
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