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1
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70349940511
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Antitumoric BE-43472 manufacture with streptomyces: H. Kushida, S. Nakajima, T. Koyama, H. Suzuki, K. Ojiri, H. Suda, JP 08143569,1996.
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"Antitumoric BE-43472 manufacture with streptomyces": H. Kushida, S. Nakajima, T. Koyama, H. Suzuki, K. Ojiri, H. Suda, JP 08143569,1996.
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2
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33747422504
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a) A. M. Socha, D. Garcia, R. Sheffer, D. C. Rowley, J. Nat. Prod. 2006, 69, 1070.
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J. Nat. Prod
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Socha, A.M.1
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b) A. M. Socha, K. L. LaPlante, D. C. Rowley, Bioorg. Med. Chem. 2006, 14, 8446.
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Bioorg. Med. Chem
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Socha, A.M.1
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4
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47749093130
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For recent reviews on this topic, see: a
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For recent reviews on this topic, see: a) G. Taubes, Science 2008, 321, 356.
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Science
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Taubes, G.1
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5
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70349938890
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K. C. Nicolaou, J. S. Chen, D. J. Edmonds, A. A. Estrada, Angew. Chem. 2009, 121, 670; Angew. Chem. Int. Ed. 2009, 48, 660.
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b) K. C. Nicolaou, J. S. Chen, D. J. Edmonds, A. A. Estrada, Angew. Chem. 2009, 121, 670; Angew. Chem. Int. Ed. 2009, 48, 660.
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6
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70349937245
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For previous synthetic studies inspired by BE-43472B, see: a K. Suzuki, H. Takikawa, Y. Hachisu, J. W. Bode, Angew. Chem. 2007, 119, 3316;
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For previous synthetic studies inspired by BE-43472B, see: a) K. Suzuki, H. Takikawa, Y. Hachisu, J. W. Bode, Angew. Chem. 2007, 119, 3316;
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8
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70349963812
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H. Takikawa, K. Hikita, K. Suzuki, Angew. Chem. 2008, 120, 10035 Angew. Chem. Int. Ed. 2008, 47, 9887.
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b) H. Takikawa, K. Hikita, K. Suzuki, Angew. Chem. 2008, 120, 10035 Angew. Chem. Int. Ed. 2008, 47, 9887.
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10
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70349938892
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E. J. Corey, Angew. Chem. 2002, 114, 1724; Angew. Chem. Int. Ed. 2002, 41, 1650.
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b) E. J. Corey, Angew. Chem. 2002, 114, 1724; Angew. Chem. Int. Ed. 2002, 41, 1650.
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11
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70349960907
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K. C. Nicolaou, Angew. Chem. 2002, 114, 1742; Angew. Chem. Int. Ed. 2002, 41, 1668.
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K. C. Nicolaou, Angew. Chem. 2002, 114, 1742; Angew. Chem. Int. Ed. 2002, 41, 1668.
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12
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33645396909
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J. A. Marshall, M. M. Yanik, N. D. Adams, K. C. Ellis, H. R. Chobanian, Org. Synth. 2005, 81, 157.
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Org. Synth
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Marshall, J.A.1
Yanik, M.M.2
Adams, N.D.3
Ellis, K.C.4
Chobanian, H.R.5
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15
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33750997236
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a) K. C. Nicolaou, Y. H. Lim, C. D. Papageorgiou, J. L. Piper, Angew. Chem. 2005, 117, 8131;
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Angew. Chem
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Nicolaou, K.C.1
Lim, Y.H.2
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Piper, J.L.4
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34247141018
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b) K. C. Nicolaou, Y. H. Lim, J. L. Piper, C. D. Papageor- giou, J. Am. Chem. Soc. 2007, 129, 4001.
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J. Am. Chem. Soc
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Nicolaou, K.C.1
Lim, Y.H.2
Piper, J.L.3
Papageor- giou, C.D.4
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19
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0000648235
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For Diels-Alder reactions with substituted naphthoquinones, see: a
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For Diels-Alder reactions with substituted naphthoquinones, see: a) B. M. Trost, J. Ippen, W. C. Vladuchick, J. Am. Chem. Soc. 1977, 99, 8116.
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J. Am. Chem. Soc
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Trost, B.M.1
Ippen, J.2
Vladuchick, W.C.3
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20
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0011651254
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b) R. K. Boeckman, Jr., T. M. Dolak, K. O. Culos, J. Am. Chem. Soc. 1978, 100, 7098.
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J. Am. Chem. Soc
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Boeckman Jr., R.K.1
Dolak, T.M.2
Culos, K.O.3
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22
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0001623290
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M. D. Rozeboom, I.-M. Tegmo-Larsson, K. N. Houk, J. Org. Chem. 1981, 46, 2338.
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(1981)
J. Org. Chem
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Rozeboom, M.D.1
Tegmo-Larsson, I.-M.2
Houk, K.N.3
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23
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34047232186
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e) L. F. Tietze, K. M. Gericke, R. R. Singidi, I. Schuberth, Org. Biomol. Chem. 2007, 5, 1191.
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Org. Biomol. Chem
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Tietze, L.F.1
Gericke, K.M.2
Singidi, R.R.3
Schuberth, I.4
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24
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0003586413
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For a discussion of transition states of Diels-Alder reactions with chiral 1,3-dienes, see a P. G. McDougal, J. M. Jump, C. Rojas, J. G. Rico, Tetrahedron Lett. 1989, 30, 3897
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For a discussion of transition states of Diels-Alder reactions with chiral 1,3-dienes, see a) P. G. McDougal, J. M. Jump, C. Rojas, J. G. Rico, Tetrahedron Lett. 1989, 30, 3897
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25
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18844480311
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b) M. C. Carreno, S. Garcia-Cerrada, A. Urbano, C. Di Vitta, J. Org. Chem. 2000, 65, 4355.
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J. Org. Chem
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Carreno, M.C.1
Garcia-Cerrada, S.2
Urbano, A.3
Di Vitta, C.4
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26
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0037459728
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L. Barriault, J. D. O. Thomas, R. Clement, J. Org. Chem. 2003, 68, 2317.
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(2003)
J. Org. Chem
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Barriault, L.1
Thomas, J.D.O.2
Clement, R.3
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27
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70349940535
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The rather puzzling exquisite regiochemical outcome of this Diels-Alder reaction cannot be fully explained at this time, and studies directed toward its further understanding are continuing. It should be noted, however, that that a diene corresponding to 4 with a MEM-O group at its C-1 terminus (rather than a TBS-O group at its C-2 position) reacted with dienophile 5 to give exclusively the opposite regioisomeric Diels-Alder product. Further details will be reported in the full account of this work
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The rather puzzling exquisite regiochemical outcome of this Diels-Alder reaction cannot be fully explained at this time, and studies directed toward its further understanding are continuing. It should be noted, however, that that a diene corresponding to 4 with a MEM-O group at its C-1 terminus (rather than a TBS-O group at its C-2 position) reacted with dienophile 5 to give exclusively the opposite regioisomeric Diels-Alder product. Further details will be reported in the full account of this work.
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28
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70349951500
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An alternative, but less likely, mechanism for the conversion of2 to 22/epi-22 may involve initial oxonium ion formation followed by intramolecular attack from the nearby MeO group and extrusion of MeOH.
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An alternative, but less likely, mechanism for the conversion of2 to 22/epi-22 may involve initial oxonium ion formation followed by intramolecular attack from the nearby MeO group and extrusion of MeOH.
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29
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0007260358
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For examples of intermolecular SN(Ar) ipso substitution of a MeO group by carbon nucleophiles, see: a) R. C. Fuson, S. B. Speck, J. Am. Chem. Soc. 1942, 64, 2446
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N(Ar) ipso substitution of a MeO group by carbon nucleophiles, see: a) R. C. Fuson, S. B. Speck, J. Am. Chem. Soc. 1942, 64, 2446.
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31
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0035537548
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Reviews
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S. Aki, Y. Haraguchi, H. Sakikawa, M. Ishigami, T. Fujioka, T. Furuta, J.-I. Minikawa, Org. Process Res. Dev. 2001, 5, 535; Reviews:
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(2001)
Org. Process Res. Dev
, vol.5
, pp. 535
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Aki, S.1
Haraguchi, Y.2
Sakikawa, H.3
Ishigami, M.4
Fujioka, T.5
Furuta, T.6
Minikawa, J.-I.7
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33
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33947449188
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N(Ar) ipso substitution of a MeO group by an oxygen nucleophile. For the introduction of the term ipso substitution, see:
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N(Ar) ipso substitution of a MeO group by an oxygen nucleophile. For the introduction of the term ipso substitution, see:
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35
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70349975095
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Since epimers 22 and epi-22 are hardly separable and because the subsequent intermediates 23 and 24 were also shown to epimerize under the reaction conditions employed for their generation, it was more expedient and efficient to carry the mixture of epi-22 and 22 through the three-step sequence and separate the obtained enone 25 and its C-3 epimer epi-25 by chromatography.
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Since epimers 22 and epi-22 are hardly separable and because the subsequent intermediates 23 and 24 were also shown to epimerize under the reaction conditions employed for their generation, it was more expedient and efficient to carry the mixture of epi-22 and 22 through the three-step sequence and separate the obtained enone 25 and its C-3 epimer epi-25 by chromatography.
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36
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70349937272
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CCDC 714178 (25) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data-request/cif.
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CCDC 714178 (25) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data-request/cif.
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37
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70349938909
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In the initial synthesis of, we also obtained the X-ray crystal structure of ent-25. CCDC 711967 (ent-25) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallo- graphic Data Centre via
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In the initial synthesis of (-we also obtained the X-ray crystal structure of ent-25. CCDC 711967 (ent-25) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallo- graphic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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40
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Interestingly, the minor epimeric oxirane epi-28 remained unchanged under the same photolytic conditions.
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Interestingly, the minor epimeric oxirane epi-28 remained unchanged under the same photolytic conditions.
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43
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84890766709
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Wiley-VCH, Weinheim
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b) L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006, p. 672.
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(2006)
Domino Reactions in Organic Synthesis
, pp. 672
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Tietze, L.F.1
Brasche, G.2
Gericke, K.3
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K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292;
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(2006)
Angew. Chem
, vol.118
, pp. 7292
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Nicolaou, K.C.1
Edmonds, D.J.2
Bulger, P.G.3
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