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Wessels, P.L.5
Hull, W.E.6
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For the first total synthesis of penitrem D, see: (a) Smith, A. B., III; Kanoh, N.; Ishiyama, H.; Hartz, R. A. J. Am. Chem. Soc. 2000, 122, 11254-11255.
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(b) Kanoh, N.; Smith, A. B., III; Ishiyama, H.; Minakawa, N.; Rainier, J. D.; Hartz, R. A.; Cho, Y. S.; Cui, H.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 8228-8237.
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Smith III, A.B.2
Ishiyama, H.3
Minakawa, N.4
Rainier, J.D.5
Hartz, R.A.6
Cho, Y.S.7
Cui, H.8
Moser, W.H.9
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5
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For a recent communication of our synthetic work in this area, see: Rivkin, A.; Nagashima, T.; Curran, D. P. Org. Lett. 2003, 5, 419-422.
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Nagashima, T.2
Curran, D.P.3
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0011204990
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Zard, S. Z., Ed.; Jai Press: Stamford, CT
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We use here the "radical/polar crossover" terminology of Murphy, but such reactions are also called by other names such as "cascade radical/ionic reactions". Bashir, N.; Patro, B.; Murphy, J. A. Advances In Free Radical Chemistry; Zard, S. Z., Ed.; Jai Press: Stamford, CT, 1999; Vol. 2, pp 123-150.
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Advances in Free Radical Chemistry
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Bashir, N.1
Patro, B.2
Murphy, J.A.3
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7
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85039535136
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Ph.D. Thesis, University of Pittsburgh
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(a) Nagashima, T. Ph.D. Thesis, University of Pittsburgh, 1999.
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Nagashima, T.1
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Ph.D. Thesis, University of Pittsburgh
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(b) Rivkin, A. Ph.D. Thesis, University of Pittsburgh, 2001.
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Rivkin, A.1
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Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
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(d) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 779-831.
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(e) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961.
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Synlett.
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Curran, D.P.1
Fevig, T.L.2
Jasperse, C.P.3
Totleben, M.J.4
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15
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0042789931
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For example, the ketone group of cyclobutanones has often been used in radical cyclization reactions: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Cyclizations to methylene cyclobutanes are also known: Zhang, W.; Dowd, P. Tetrahedron Lett. 1995, 36, 8539-8542.
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Chem. Rev.
, vol.93
, pp. 2091-2115
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Dowd, P.1
Zhang, W.2
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16
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0028866090
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For example, the ketone group of cyclobutanones has often been used in radical cyclization reactions: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Cyclizations to methylene cyclobutanes are also known: Zhang, W.; Dowd, P. Tetrahedron Lett. 1995, 36, 8539-8542.
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Tetrahedron Lett.
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, pp. 8539-8542
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Zhang, W.1
Dowd, P.2
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17
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0342369341
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Examples of radical additions to cyclobutenes: (a) Ferjanč ić, Z.; Čeković, Z.; Saičić, R. N. Tetrahedron Lett. 2000, 41, 2979-2982.
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Tetrahedron Lett.
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Ferjančić, Z.1
Čeković, Z.2
Saičić, R.N.3
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18
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0028944101
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(b) Campbell, E. F.; Park, A. K.; Kinney, W. A.; Fengl, R. W.; Liebeskind, L. S. J. Org. Chem. 1995, 60, 1470-1472.
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Campbell, E.F.1
Park, A.K.2
Kinney, W.A.3
Fengl, R.W.4
Liebeskind, L.S.5
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19
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0034627386
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(c) Legrand, N.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 2000, 41, 9815-9818.
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Tetrahedron Lett.
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Legrand, N.1
Quiclet-Sire, B.2
Zard, S.Z.3
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20
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0037150326
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(d) Chen, X.-P.; Sufi, B. A.; Padias, A. B.; Hall, H. K., Jr. Macromolecules 2002, 35, 4277-4281.
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Macromolecules
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Chen, X.-P.1
Sufi, B.A.2
Padias, A.B.3
Hall Jr., H.K.4
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21
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85039525817
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note
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A detailed description of the syntheses can be found in Supporting Information. See also Supporting Information of ref 3.
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22
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85039520363
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note
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The relative stereochemistry of the syn-27 and anti-27 precursors was assigned on the basis of the relative stereochemistry of the corresponding cyclized products 38 and 40 (these were assigned by analysis of the coupling constant between the secondary benzylic hydrogens and the neighboring tertiary silyl ether hydrogen).
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23
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0027538424
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(a) Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
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Tetrahedron
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Newcomb, M.1
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26
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0001360724
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(d) Johnston, L. J.; Lusztyk, J.; Wayner, D. D. M.; Abeywickrema, A. N.; Beckwith, A. L. J.; Scaiano, J. C.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 4594-4596.
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Lusztyk, J.2
Wayner, D.D.M.3
Abeywickrema, A.N.4
Beckwith, A.L.J.5
Scaiano, J.C.6
Ingold, K.U.7
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29
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0000955889
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(g) Garden, S. J.; Avila, D. V.; Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U.; Lusztyk, J. J. Org. Chem. 1996, 61, 805-809.
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Avila, D.V.2
Beckwith, A.L.J.3
Bowry, V.W.4
Ingold, K.U.5
Lusztyk, J.6
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31
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0037419357
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For a discussion of the influence of ortho substituents in radical mediated cyclizations, see: Curran, D. P.; Fairweather, N. J. Org. Chem. 2003, 68, 2972-2974.
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Curran, D.P.1
Fairweather, N.2
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32
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85039520756
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note
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Configurations were tentatively assigned on the basis of the observation of a trans-diaxial coupling constant (11 Hz) between the proton adjacent to the OTBS group and one of the benzylic methylene protons in anti-27. Both modeling and the crystal structure of 54 indicated a dihedral angle of close to 180° in this isomer.
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33
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0004145743
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VCH: Weinheim
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Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: Weinheim, 1996.
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Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications
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Curran, D.P.1
Porter, N.A.2
Giese, B.3
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34
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85039526564
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note
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Experiment performed in the cyclized products 48 and 50.
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35
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0542358061
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Examples of Heck cyclizations: (a) Zhang, Y.; O'Conner, B.; Negishi, E. J. Org. Chem. 1988, 53, 5590-5592.
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J. Org. Chem.
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Zhang, Y.1
O'Conner, B.2
Negishi, E.3
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36
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0001393289
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(b) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 24, 2919-2922.
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(1988)
Tetrahedron Lett.
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, pp. 2919-2922
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Larock, R.C.1
Song, H.2
Baker, B.E.3
Gong, W.H.4
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38
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0343343243
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(d) Negishi, E.; Zhang, Y.; O'Conner, B. Tetrahedron Lett. 1988, 24, 2915-2918.
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Tetrahedron Lett.
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Negishi, E.1
Zhang, Y.2
O'Conner, B.3
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39
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0027300192
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(e) Grigg, R.; Santhakumar, V.; Sridharan, V. Tetrahedron Lett. 1993, 34, 3163-3164.
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Tetrahedron Lett.
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Grigg, R.1
Santhakumar, V.2
Sridharan, V.3
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40
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0026741629
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(f) Torii, S.; Okumoto, H.; Ozaki, H.; Nakayasu, S.; Tadokoro, T.; Kotani, T. Tetrahedron Lett. 1992, 24, 3499-3502.
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Tetrahedron Lett.
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Torii, S.1
Okumoto, H.2
Ozaki, H.3
Nakayasu, S.4
Tadokoro, T.5
Kotani, T.6
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