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(c) Snyder, N. L.; Haines, H. M.; Peczuh, M. W. Tetrahedron 2006, 62, 9301-9320.
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(d) Inoue, M. Chem. Rev. 2005, 105, 4379-4405.
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(a) Marmsäter, F. P.; Vanecko, J. A.; West, F. G. Tetrahedron 2002, 58, 2027-2040.
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West, F.G.3
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10
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0000517783
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For an alternative two-carbon intercalation process involving the addition of simple acetylides to lactones or lactams followed by endocyclization, see: (a) Schreiber, S. L.; Kelly, S. E. Tetrahedron Lett. 1984, 25, 1757-1760.
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For an alternative two-carbon intercalation process involving the addition of simple acetylides to lactones or lactams followed by endocyclization, see: (a) Schreiber, S. L.; Kelly, S. E. Tetrahedron Lett. 1984, 25, 1757-1760.
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(b) Schreiber, S. L.; Kelly, S. E.; Porco, J. A., Jr.; Sammakia, T.; Suh, E. M. J. Am. Chem. Soc. 1988, 110, 6210-6218.
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Schreiber, S.L.1
Kelly, S.E.2
Porco Jr., J.A.3
Sammakia, T.4
Suh, E.M.5
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(c) Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. J. Org. Chem. 1987, 52, 2929-2930.
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Suzuki, K.1
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Tsuchihashi, G.3
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(b) Comins, D. L.; Huang, S.; McArdle, C. L.; Ingalls, C. L. Org. Lett. 2001, 3, 469-471.
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33750118232
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(a) Yamaguchi, M.; Shibato, K.; Fujiwara, S.; Hirao, L. Synthesis 1986, 421-422.
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Yamaguchi, M.1
Shibato, K.2
Fujiwara, S.3
Hirao, L.4
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17
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(b) Krafft, M. E.; Boñaga, L. V. R.; Felts, A. S.; Hirosawa, C.; Kerrigan, S. J. Org. Chem. 2003, 68, 6039-6042.
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Krafft, M.E.1
Boñaga, L.V.R.2
Felts, A.S.3
Hirosawa, C.4
Kerrigan, S.5
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18
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(c) Doubsky, J.; Streinz, L.; Leseticky, L.; Koutek, B. Synlett 2003, 7, 937-942.
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Doubsky, J.1
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Koutek, B.4
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(d) Doubsky, J.; Streinz, L.; Saman, D.; Zednik, J.; Koutek, B. Org. Lett. 2004, 6, 4909-4911.
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(b) Stefani, H. A.; Cella, R.; Vieira, A. S. Tetrahedron 2007, 63, 3623-3658.
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Stefani, H.A.1
Cella, R.2
Vieira, A.S.3
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A similar explanation was given for the superiority of the Keck lactonization conditions (DMAP/DMAP-HCl): (a) Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394-2395.
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A similar explanation was given for the superiority of the Keck lactonization conditions (DMAP/DMAP-HCl): (a) Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394-2395.
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See also
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(b) See also: Spivey, A. C.; Arseniyadis, S. Angew. Chem., Int. Ed. 2004, 43, 5436-5441.
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(2004)
Angew. Chem., Int. Ed
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Spivey, A.C.1
Arseniyadis, S.2
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35048856419
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Gabillet, S.; Lecerclé, D.; Loreau, O.; Carboni, M.; Dézard, S.; Gomis, J.-M.; Taran, F. Org. Lett. 2007, 9, 3925-3927.
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(2007)
Org. Lett
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Gabillet, S.1
Lecerclé, D.2
Loreau, O.3
Carboni, M.4
Dézard, S.5
Gomis, J.-M.6
Taran, F.7
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61349156489
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The seven-membered product 3b could not easily be distinguished from the alternative isomeric structure 8b by standard 1D NMR techniques. However, HMBC experiments clearly indicated a correlation between H-4 and C-2, which would not be observable in 8b (see Scheme 2).
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The seven-membered product 3b could not easily be distinguished from the alternative isomeric structure 8b by standard 1D NMR techniques. However, HMBC experiments clearly indicated a correlation between H-4 and C-2, which would not be observable in 8b (see Scheme 2).
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26
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61349171014
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1H NMR chemical shifts of the alkene proton to those of 3fZ and 3fE as well as related literature compounds. See Supporting Information for a discussion of these assignments.
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1H NMR chemical shifts of the alkene proton to those of 3fZ and 3fE as well as related literature compounds. See Supporting Information for a discussion of these assignments.
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27
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61349132614
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A vicinal coupling of 9.5 Hz between the adjacent ester-substituted methines was observed, consistent with a trans relationship. See Supporting Information for additional discussion of structural assignments.
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A vicinal coupling of 9.5 Hz between the adjacent ester-substituted methines was observed, consistent with a trans relationship. See Supporting Information for additional discussion of structural assignments.
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61349105077
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The connectivity of endocyclization products 8g,h was established via HMBC correlations between the alkene proton (H-3) and C-5.
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The connectivity of endocyclization products 8g,h was established via HMBC correlations between the alkene proton (H-3) and C-5.
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37049046169
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For earlier examples of similar pyridine-ynone adducts, see: a
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For earlier examples of similar pyridine-ynone adducts, see: (a) Crabtree, A.; Jackman, L. M.; Johnson, A. W. J. Chem. Soc. 1962, 4417-4420.
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(1962)
J. Chem. Soc
, pp. 4417-4420
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Crabtree, A.1
Jackman, L.M.2
Johnson, A.W.3
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(c) Acheson, R. M.; Wallis, J. D.; Woollard, J. J. Chem. Soc., Perkin Trans. 1 1979, 584-590.
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(1979)
J. Chem. Soc., Perkin Trans. 1
, pp. 584-590
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Acheson, R.M.1
Wallis, J.D.2
Woollard, J.3
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