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0041878683
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For recent reviews see: (a) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263. (b) Bar, G.; Parsons, A. F. Chem. Soc. Rev. 2003, 32, 251. (c) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. (d) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8303.
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Sibi, M.P.1
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For recent reviews see: (a) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263. (b) Bar, G.; Parsons, A. F. Chem. Soc. Rev. 2003, 32, 251. (c) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. (d) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8303.
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Bar, G.1
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For recent reviews see: (a) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263. (b) Bar, G.; Parsons, A. F. Chem. Soc. Rev. 2003, 32, 251. (c) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. (d) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8303.
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Sibi, M.P.1
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Racemic synthesis: (a) Agapiou, K.; Krische, M. J. Org. Lett. 2003, 5, 1737. (b) Takeda, K.; Ohkawa, N.; Hori, K.; Koizumi, T.; Yoshii, E. Heterocycles 1998, 47, 277.
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26
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2942526199
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note
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A similar disconnection has been applied in the racemic synthesis of 1 starting with 3 (or a slight variant) and 3-furyllithium (see refs 5b-e). The yield for this transformation has been <30%.
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27
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2942595039
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These compounds were prepared in a straightforward fashion using well-established literature procedures. See Supporting Information for details
-
These compounds were prepared in a straightforward fashion using well-established literature procedures. See Supporting Information for details.
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28
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2942531481
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See Supporting Information for details
-
See Supporting Information for details.
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29
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2942527958
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note
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2 has been previously shown to provide products with R configuration. We initially assigned the stereochemistry for 16 on the basis of the above precedents, which was later confirmed by the synthesis of the natural product.
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30
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0035031177
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(a) Orita, A.; Nagano, Y.; Hirano, J.; Otera, J. Synlett 2001, 637.
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Orita, A.1
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31
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(b) Also see: Sibi, M. P.; Hasegawa, H.; Ghorpade, S. R. Org. Lett. 2002, 4, 3343.
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32
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note
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Attempts to form the six-membered ring with an acyl-oxazolidinone (instead of the methyl ester) gave complex product mixtures.
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-
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33
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2942555884
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note
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d = 3.6 Hz, 1H). The 12 Hz coupling constant clearly establishes the relative stereochemistry at the ring as trans.
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34
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2942614048
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note
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Temperature of the reaction is important to avoid the premature formation of the lactone.
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35
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0031585678
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For the addition of 3-furyllithium to aliphatic aldehydes, see: (a) Corey, E. J.; Roberts, B. E. J. Am. Chem. Soc. 1997, 119, 12425. (b) Demeke. D.; Forsyth, C. J. Org. Lett. 2000, 2, 3177. (c) Takahashi, M.; Dodo, K.; Hashimoto, Y.; Shirai, R. Tetrahedron Lett. 2000, 41, 2111. (d) Liu, H.-J.; Zhu, J.-L.; Chen, I.-C.; Jankowska, R.; Han, Y.; Shia, K.-S. Angew. Chem., Int. Ed. 2003, 42, 1851.
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Corey, E.J.1
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36
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0034609670
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For the addition of 3-furyllithium to aliphatic aldehydes, see: (a) Corey, E. J.; Roberts, B. E. J. Am. Chem. Soc. 1997, 119, 12425. (b) Demeke. D.; Forsyth, C. J. Org. Lett. 2000, 2, 3177. (c) Takahashi, M.; Dodo, K.; Hashimoto, Y.; Shirai, R. Tetrahedron Lett. 2000, 41, 2111. (d) Liu, H.-J.; Zhu, J.-L.; Chen, I.-C.; Jankowska, R.; Han, Y.; Shia, K.-S. Angew. Chem., Int. Ed. 2003, 42, 1851.
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Demeke, D.1
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For the addition of 3-furyllithium to aliphatic aldehydes, see: (a) Corey, E. J.; Roberts, B. E. J. Am. Chem. Soc. 1997, 119, 12425. (b) Demeke. D.; Forsyth, C. J. Org. Lett. 2000, 2, 3177. (c) Takahashi, M.; Dodo, K.; Hashimoto, Y.; Shirai, R. Tetrahedron Lett. 2000, 41, 2111. (d) Liu, H.-J.; Zhu, J.-L.; Chen, I.-C.; Jankowska, R.; Han, Y.; Shia, K.-S. Angew. Chem., Int. Ed. 2003, 42, 1851.
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Takahashi, M.1
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38
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0037693737
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For the addition of 3-furyllithium to aliphatic aldehydes, see: (a) Corey, E. J.; Roberts, B. E. J. Am. Chem. Soc. 1997, 119, 12425. (b) Demeke. D.; Forsyth, C. J. Org. Lett. 2000, 2, 3177. (c) Takahashi, M.; Dodo, K.; Hashimoto, Y.; Shirai, R. Tetrahedron Lett. 2000, 41, 2111. (d) Liu, H.-J.; Zhu, J.-L.; Chen, I.-C.; Jankowska, R.; Han, Y.; Shia, K.-S. Angew. Chem., Int. Ed. 2003, 42, 1851.
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Liu, H.-J.1
Zhu, J.-L.2
Chen, I.-C.3
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Han, Y.5
Shia, K.-S.6
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For the addition of 3-furylmagnesium bromide to imines, see: (a) Plobeck, N.; Powell, D. Tetrahedron: Asymmetry 2002, 13, 303. (b) Oppolzer, W.; Froelich, O.; Wiaux-Zamar, C.; Bernardinelli, G. Tetrahedron Lett. 1997, 37, 2825.
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Plobeck, N.1
Powell, D.2
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40
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0031006429
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For the addition of 3-furylmagnesium bromide to imines, see: (a) Plobeck, N.; Powell, D. Tetrahedron: Asymmetry 2002, 13, 303. (b) Oppolzer, W.; Froelich, O.; Wiaux-Zamar, C.; Bernardinelli, G. Tetrahedron Lett. 1997, 37, 2825.
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Oppolzer, W.1
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41
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Preparation of 3-furylzinc reagent: Negishi, E.-i.; Takahashi, T.; King, A. O. Org. Synth. 1988, 66, 67.
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Difuryl zinc reagents: Xue, S.; Han, K.-Z.; He, L.; Guo, Q.-X. Synlett 2003, 870.
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Xue, S.1
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For a recent review, see: (b) Cossy, J.; BouzBouz, S.; Pradaux, F.; Willis, C.; Bellosta, V. Synlett 2002, 1595.
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