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For the synthesis of cycloheptane derivatives from carbohydrates, see: (a) Marco-contelles, J.; de Opazo, E. Tetrahedron Lett. 1999, 40, 4445; Tetrahedron Lett. 2000, 41, 2439.
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For the synthesis of cyclooctane derivatives from sugars, see ret 2b and Werschkum, B.; Thiem, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2793.
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For earlier examples of cyclooctene syntheses by RCM, see: ref 6. For more recent applications, see: (a) Paquette, L. A.; Schloss, J. D.; Efremov, I.; Fabris, F.; Gallou, F.; Méndez-Andino, J. Yang, J. Org. Lett. 2000, 2, 1259.
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and references therein
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(b) Paquette, L. A.; Tae, J.; Arrington, M. P.; Sadoun, A. H. J. Am. Chem. Soc. 2000, 122, 2742 and references therein
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(c) Bourgeois, D.; Pancrazi, A.; Ricard, L. P.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 726. For recent reports on the syntesis of cyclic ethers of eight-membered ring, see: Clark, J. S.; Mamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372. Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653.
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(c) Bourgeois, D.; Pancrazi, A.; Ricard, L. P.; Prunet, J. Angew. Chem., Int. Ed. 2000, 39, 726. For recent reports on the syntesis of cyclic ethers of eight-membered ring, see: Clark, J. S.; Mamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372. Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653.
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26
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15844382728
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Compound 10 is readily prepared by iodation of the commercially available 1.2:3,4-di-O-isopropylidene-D-galactopyranose: Garegg, P. J.; Johansson, R.; Ortega, C.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1982, 681.
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Samuelsson, B.4
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27
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85037510938
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note
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All new compounds were characterized by analytical and spectroscopic data. Yields are for isolated, chromatographically purified products.
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28
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85037517328
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note
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See ref 2e. We thank professor Robert Madsen for experimental details for the preparation of amino diene 4.
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29
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85037516579
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note
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Table 2 in ref 6b points to the ease of closing seven-membered monocycles as compared with the formation of cyclooctenes.
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See ref 3 and Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297. Johnson, C. R.; Bis, S. J. J. Org. Chem. 1995, 60, 615.
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Katiyar, S.2
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See ref 3 and Pearson, A. J.; Katiyar, S. Tetrahedron 2000, 56, 2297. Johnson, C. R.; Bis, S. J. J. Org. Chem. 1995, 60, 615.
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Johnson, C.R.1
Bis, S.J.2
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