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total synthesis of (+)-cylindricines C, D, and E: b) B. M. Trost, M. T. Rudd, Org. Lett. 2003, 5, 4599;
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total synthesis of (±)-cylindricines A, D, and E: c) B. B. Snider, T. Liu, J. Org. Chem. 1997, 62, 5630;
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Snider, B.B.1
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synthesis of (±)-4-epicylindricine C: e) K. M. Werner, J. M. de los Santos, S. M. Weinreb, M. Shang, J. Org. Chem. 1999, 64, 4865;
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g) W. H. Pearson, N. S. Barta, J. W. Kamp, Tetrahedron Lett. 1997, 38, 3369.
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Pearson, W.H.1
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0034679048
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For synthetic studies on the structurally related alkaloids, fasicularin and lepadiformine, see: a) H. Abe, S. Aoyagi, C. Kibayashi, J. Am. Chem. Soc. 2000, 122, 4583;
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e) H. Abe, S. Aoyagi, C. Kibayashi, Angew. Chem. 2002, 114, 3143, Angew. Chem. Int. Ed. 2002, 41, 3017;
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e) H. Abe, S. Aoyagi, C. Kibayashi, Angew. Chem. 2002, 114, 3143, Angew. Chem. Int. Ed. 2002, 41, 3017;
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h) C. Kibayashi, S. Aoyagi, H. Abe, Bull. Chem. Soc. Jpn. 2003, 76, 2059;
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Kibayashi, C.1
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note
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Unpublished results from these laboratories; details will be provided in a forthcoming full paper.
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note
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[3a]
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4544333276
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note
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2/MeOH;
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25
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note
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2, 0 °C, (formation of the N,O-dimesyl derivative), 91% over two steps;
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26
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4544346683
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note
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4/EtOH/THF, 94%;
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27
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note
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d) NaOH/dioxane, 80 °C, 90%. Ms = methanesulfonyl, TEA = triethylamine.
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28
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note
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Under identical conditions, cyclization of the corresponding methyl ether proceeded with d.r. = 3.5:1 and that of the TBDMS ether with d.r. = 4.5:1.
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0003942864
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Wiley, New York
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The structure of this material was confirmed by an X-ray crystallographic study of its desilylated analogue. The selectivity of the 1,4-addition of PhSH to 8 appears to be due to a Felkin-Anh-type stereoelectronic effect created by the strongly electro-negative sulfonamide nitrogen atom. For examples, see: a) E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 875;
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(1994)
Stereochemistry of Organic Compounds
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Eliel, E.L.1
Wilen, S.H.2
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0034638792
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and references therein
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b) S. Bennabi, K. Narkunan, L. Rousset, D. Bouchu, M. A. Ciufolini, Tetrahedron Lett. 2000, 41, 8873, and references therein.
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Bennabi, S.1
Narkunan, K.2
Rousset, L.3
Bouchu, D.4
Ciufolini, M.A.5
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R. Mozingo, D. E. Wolf, S. A. Harris, K. Folkers, J. Am. Chem. Soc. 1943, 65, 1013.
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Mozingo, R.1
Wolf, D.E.2
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Folkers, K.4
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32
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0035906463
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Weaker bases were ineffective for deprotonation of 10, in accord with: L. A. Paquette, S. C. Ra, J. D. Schloss, S. M. Leit, J. C. Gallucci, J. Org. Chem. 2001, 66, 3564.
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Paquette, L.A.1
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33
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33845469694
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a) M. J. Eis, J. E. Wrobel, B. Ganem, J. Am. Chem. Soc. 1984, 106, 3693;
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K. Takahashi, T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2001, 625, 47.
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Takahashi, K.1
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37
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4544348292
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note
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13C NMR (75 MHz) spectrometry.
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38
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0009616804
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For amine-directed organocuprate additions, see: a) D. K. Hutchinson, S. A. Hardinger, P. L. Fuchs, Tetrahedron Lett. 1986, 27, 1425;
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(1986)
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Hutchinson, D.K.1
Hardinger, S.A.2
Fuchs, P.L.3
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39
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0034724768
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b) for an excellent bibliography on general directed organocuprate addition reactions,see: B. Breit, P. Demel, Tetrahedron 2000, 56, 2833.
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(2000)
Tetrahedron
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Breit, B.1
Demel, P.2
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4544254526
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note
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For related processes, see reference [3g].
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42
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4544279165
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note
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[3e] (see Supporting Information).
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43
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0025364262
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D. A. Evans, J. S. Clark, R. Metternich, V. J. Novack, G. S. Sheppard, J. Am. Chem. Soc. 1990, 112, 866.
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Evans, D.A.1
Clark, J.S.2
Metternich, R.3
Novack, V.J.4
Sheppard, G.S.5
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4544243758
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note
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2) for reference [3a].
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