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For recent reviews, see: a) M. C. McMills, D. Wright in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products (Eds.: A. Padwa, W. H. Pearson), Wiley, New York, 2002, pp. 253-314;
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0024827695
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For representative works on the related [5+2] cycloadditions between oxypyrylium ylides and alkenes, see: a) P. A. Wender, H. Y. Lee, R. S. Wilhelm, P. D. Williams, J. Am. Chem. Soc. 1989, 111, 8954-8957;
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33749869983
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c) W. E. Bauta et al., see Supporting Information;
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0032949054
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28
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33749836515
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note
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The homochirality of ketone 7 and cycloadduct 3 was confirmed by HPLC on a chiral stationary phase.
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29
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0010497656
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W. J. Elliott, J. Fried, J. Org. Chem. 1978, 43, 2708-2710. We thank a referee for bringing the reference to our attention.
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33749871372
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note
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4 at room temperature to provide a 1:1 mixture of diastereomeric cycloadducts in 35 % yield, indicating that carbonyl ylide 5 was formed under these conditions. Heating is required to promote the intramolecular cycloaddition with a nonactivated alkene.
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31
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33749822413
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note
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4 (41%).
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-
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32
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0033576992
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II-catalyzed carbonyl ylide formation/1,3-dipolar cycloaddition reactions, see: S. Kitagaki, M. Anada, O. Kataoka, K. Matsuno, C. Umeda, N. Watanabe, S. Hashimoto, J. Am. Chem. Soc. 1999, 121, 1417-1418.
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Hashimoto, S.7
-
33
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33749861664
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note
-
The cycloaddition is not scale dependent and the cycloadduct 3 was obtained in 70% yield when the reaction was performed on a 500-mg scale.
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34
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46549104605
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T. Fukuyama, A. A. Laird, L. M. Hotchkiss, Tetrahedron Lett. 1985, 26, 6291-6292.
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33847086576
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b) S. Murata, M. Suzuki, R. Noyori, J. Am. Chem. Soc. 1980, 102, 3248-3249;
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38
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33749864724
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note
-
A plausible biogenesis of polygalolides is illustrated schematically below. (Chemical Equation Presented)
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