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Cyclotryptophans have been shown to suffer oxidation at the 3a-position under free radical conditions: M. Bruncko, D. Crich, R. Samy, Heterocycles 1993, 36, 1735-1738.
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Debnath, P.K.4
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87
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0033616097
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Other means of assembling vicinal quaternary carbon centers, based on radical-radical couplings, have been disclosed: a K. M. Depew, S. P. Marsden, D. Zatorska, A. Zatorski, W. G. Bornmann, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 11953-11963;
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Other means of assembling vicinal quaternary carbon centers, based on radical-radical couplings, have been disclosed: a) K. M. Depew, S. P. Marsden, D. Zatorska, A. Zatorski, W. G. Bornmann, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 11953-11963;
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Nakagawa, M.1
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T. Hino, S. Kodato, K. Takahashi, H. Yamaguchi, M. Nakagawa, Tetrahedron Lett. 1978, 19, 4913-4916.
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Hino, T.1
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94
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34547162044
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Alternatively referred to as a dihydroisoindigo
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Alternatively referred to as a dihydroisoindigo.
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-
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97
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0000797940
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L. E. Overman, J. F. Larrow, B. A. Stearns, J. M. Vance, Angew. Chem. 2000, 112, 219-221;
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84897607213
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Angew. Chem. Int. Ed. 2000, 39, 213-215.
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Angew1
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E. A. Mash, K. A. Nelson, S. Van Deusen, S. B. Hemperly in Organic Syntheses, Coll. 8 (Ed.: J. D. White), Wiley, New York, 1993, pp. 92-103.
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E. A. Mash, K. A. Nelson, S. Van Deusen, S. B. Hemperly in Organic Syntheses, Coll. Vol. 8 (Ed.: J. D. White), Wiley, New York, 1993, pp. 92-103.
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100
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34547167138
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Ditriflate 39 has a shelf life of over one year when stored at -10°C.
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Ditriflate 39 has a shelf life of over one year when stored at -10°C.
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101
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Consistent with this interpretation, stereoselection was eroded in the presence of a sodium-selective cryptand (Kryptofix 221).
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Consistent with this interpretation, stereoselection was eroded in the presence of a sodium-selective cryptand (Kryptofix 221).
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103
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34547213447
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[71,73]
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[71,73]
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105
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0037663859
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Angew. Chem. Int. Ed. 2003, 42, 2525-2528;
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The translation of chirality from the electrophile to the quaternary stereocenter is influenced by the substituent at the 3-position of the oxindole, if LHMDS is used as the base. Intriguingly, when this substituent is changed from an oxindole enolate to a benzyl group, the quaternary stereocenter is installed in the corresponding product with the opposite relative configuration. A model to rationalize stereoinduction, when a benzyl group is the oxindole substituent has been proposed.[75
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[75]
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108
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7444242718
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A. Huang, J. J. Kodanko, L. E. Overman, J. Am. Chem. Soc. 2004, 126, 14043-14053.
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34547210854
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[71]
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[71]
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110
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0012857368
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For comprehensive recent reviews of the intramolecular Heck reaction, see: a, Ed, L. E. Overman, Wiley-VCH, Hoboken
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For comprehensive recent reviews of the intramolecular Heck reaction, see: a) J. T. Link in Organic Reactions, Vol. 60 (Ed.: L. E. Overman), Wiley-VCH, Hoboken, 2002, pp. 157-534;
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Organic Reactions
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Link, J.T.1
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111
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0037782994
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Eds, F. Diederich, P. J. Stang, Wiley-VCH, New York
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b) S. Bräse, A. de Meijere in Metal Catalysed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, pp. 99-154;
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Bräse, S.1
de Meijere in, A.2
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112
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0002654419
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Eds, F. Diederich, P. J. Stang, Wiley-VCH, New York
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c) J. T. Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, pp. 231-269;
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Metal-Catalyzed Cross-Coupling Reactions
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Link, J.T.1
Overman, L.E.2
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113
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12344334436
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For reviews focusing on catalytic asymmetric Heck reactions, see: d
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For reviews focusing on catalytic asymmetric Heck reactions, see: d) M. Shibasaki, E. M. Vogl, T. Ohshima, Adv. Synth. Catal. 2004, 346, 1533-1552;
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Adv. Synth. Catal
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Shibasaki, M.1
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114
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33644693756
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Eds, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
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e) M. Shibasaki, E. M. Vogl, T. Ohshima in Comprehensive Asymmetric Catalysis, Suppl. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 2004, pp. 73-81;
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Comprehensive Asymmetric Catalysis, Suppl. 1
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Shibasaki, M.1
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116
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0242632859
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Ed, E. Negishi, Wiley, Hoboken
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g) M. Shibasaki, F. Miyazaki in Handbook of Organopalladium Chemistry for Organic Synthesis, Suppl. 1 (Ed.: E. Negishi), Wiley, Hoboken, 2002, pp. 1283-1315;
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Handbook of Organopalladium Chemistry for Organic Synthesis, Suppl. 1
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Shibasaki, M.1
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117
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0003544583
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2nd ed, Ed, I. Ojima, Wiley-VCH, New York
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h) Y. Donde, L. E. Overman in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp. 675-698;
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Catalytic Asymmetric Synthesis
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Overman, L.E.2
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0001110108
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Eds, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
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i) M. Shibasaki, E. M. Vogl in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 457-487.
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Comprehensive Asymmetric Catalysis
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Vogl, E.M.2
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0033603864
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L. E. Overman, D. V. Paone, B. A. Stearns, J. Am. Chem. Soc. 1999, 121, 7702-7703.
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J. Am. Chem. Soc
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Overman, L.E.1
Paone, D.V.2
Stearns, B.A.3
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121
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34547143881
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Cyclizations of the ditriflate and diiodide substrates were carried out in opposite enantiomeric series. The enantiomer employed in the diiodide series is pictured
-
Cyclizations of the ditriflate and diiodide substrates were carried out in opposite enantiomeric series. The enantiomer employed in the diiodide series is pictured.
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123
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0000438986
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For the initial reports of the asymmetric intramolecular Heck reaction, see: a
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For the initial reports of the asymmetric intramolecular Heck reaction, see: a) Y. Sato, M. Sodeoka, M. Shibasaki, J. Org. Chem. 1989, 54, 4738-4739;
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J. Org. Chem
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Sato, Y.1
Sodeoka, M.2
Shibasaki, M.3
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124
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0000052196
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b) N. E. Carpenter, D. J. Kucera, L. E. Overman, J. Org. Chem. 1989, 54, 5846-5848.
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J. Org. Chem
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Carpenter, N.E.1
Kucera, D.J.2
Overman, L.E.3
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125
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34547203161
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At the outset, we entertained the possibility that this chemistry might be employed to attach a new pyrrolidino[2,3-b]indoline unit to either a preexisting pyrrolidino[2,3-b]indoline fragment or an oxindole precursor of such a unit. Both possibilities were examined. For several unanticipated reasons, the oxindole sequence turned out to be less attractive: a M. Oestreich, P. R. Dennison, J. J. Kodanko, L. E. Overman, Angew. Chem. 2001, 113, 1485-1489;
-
At the outset, we entertained the possibility that this chemistry might be employed to attach a new pyrrolidino[2,3-b]indoline unit to either a preexisting pyrrolidino[2,3-b]indoline fragment or an oxindole precursor of such a unit. Both possibilities were examined. For several unanticipated reasons, the oxindole sequence turned out to be less attractive: a) M. Oestreich, P. R. Dennison, J. J. Kodanko, L. E. Overman, Angew. Chem. 2001, 113, 1485-1489;
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126
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0035901629
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Angew. Chem. Int. Ed. 2001, 40, 1439-1442;
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Chem. Int. Ed
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A. B. Dounay, K. Hatanaka, J. J. Kodanko, M. Oestreich, L. E. Overman, L. A. Pfeifer, M. M. Weiss, J. Am. Chem. Soc. 2003, 125, 6261-6271.
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Dounay, A.B.1
Hatanaka, K.2
Kodanko, J.J.3
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Pfeifer, L.A.6
Weiss, M.M.7
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129
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22844434133
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For a recent survey of the use of palladium-catalyzed reactions in total synthesis, see
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For a recent survey of the use of palladium-catalyzed reactions in total synthesis, see: K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516-4563;
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Angew. Chem. Int. Ed. 2005, 44, 4442-4489.
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0040746033
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132
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0025007141
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b) J. C. Cochran, B. S. Bronk, K. M. Terrence, H. K. Phillips, Tetrahedron Lett. 1990, 31, 6621-6624;
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0001422640
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c) J. F. Betzer, F. Delaloge, B. Muller, A. Pancrazi, J. Prunet, J. Org. Chem. 1997, 62, 7768-7780.
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134
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a) A. Ashimori, B. Bachand, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6477-6487;
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J. Am. Chem. Soc
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Ashimori, A.1
Bachand, B.2
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Poon, D.J.4
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135
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0032496939
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b) A. Ashimori, B. Bachand, M. A. Calter, S. P. Govek, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6488-6499.
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Ashimori, A.1
Bachand, B.2
Calter, M.A.3
Govek, S.P.4
Overman, L.E.5
Poon, D.J.6
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137
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34547147552
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As this was a model study, yields for the steps in sequence depicted in
-
As this was a model study, yields for the steps in sequence depicted in Scheme 20 were not optimized.
-
20 were not optimized
-
-
Scheme1
-
139
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0000131734
-
-
For examples of Stille cross-couplings at room temperature and the effect of tri-2-furylphosphine, see: V. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585-9595;
-
For examples of Stille cross-couplings at room temperature and the effect of tri-2-furylphosphine, see: V. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585-9595;
-
-
-
-
140
-
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0000340061
-
-
For the role of CuI, see: a
-
For the role of CuI, see: a) V. Farina, S. Kapadia, B. Krishnan, C. Wang, L. S. Liebeskind, J. Org. Chem. 1994, 59, 5905-5911;
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J. Org. Chem
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Farina, V.1
Kapadia, S.2
Krishnan, B.3
Wang, C.4
Liebeskind, L.S.5
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142
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34547228348
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Ph.D. thesis, University of California, Irvine USA
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a) J. J. Kodanko, Ph.D. thesis, University of California, Irvine (USA), 2003;
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(2003)
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Kodanko, J.J.1
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143
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34547164558
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Ph.D. thesis, University of California, Irvine USA
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b) B. A. Stearns, Ph.D. thesis, University of California, Irvine (USA), 2000.
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(2000)
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Stearns, B.A.1
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144
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34547220648
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For example, this structural feature is seen in X-ray structures of physostigmine; see: Cambridge Structural Database files QIHNEA and ESIRINIO.
-
For example, this structural feature is seen in X-ray structures of physostigmine; see: Cambridge Structural Database files QIHNEA and ESIRINIO.
-
-
-
-
145
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34547161462
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We have found recently that the inclusion of tert-butanol nearly doubles the yield of the final deprotection step; L. Sung unpublished results, UC Irvine, 2007.
-
We have found recently that the inclusion of tert-butanol nearly doubles the yield of the final deprotection step; L. Sung unpublished results, UC Irvine, 2007.
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146
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0037036807
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A. D. Lebsack, J. T. Link, L. E. Overman, B. A. Stearns, J. Am. Chem. Soc. 2002, 124, 9008-9009.
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J. Am. Chem. Soc
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-
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Lebsack, A.D.1
Link, J.T.2
Overman, L.E.3
Stearns, B.A.4
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147
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34547160952
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-
A two-wheeled chariot drawn by four horses harnessed abreast, one representation of which sits atop Berlin's Brandenburg Gate.
-
A two-wheeled chariot drawn by four horses harnessed abreast, one representation of which sits atop Berlin's Brandenburg Gate.
-
-
-
-
148
-
-
34547159392
-
-
This number results from excluding less-stable stereoisomers in which the pyrrolidino[2,3-b]indoline rings are trans-fused
-
This number results from excluding less-stable stereoisomers in which the pyrrolidino[2,3-b]indoline rings are trans-fused.
-
-
-
-
149
-
-
0033597606
-
-
For another example, see
-
For another example, see: E. Vedejs, O. Daugulis, J. Am. Chem. Soc. 1999, 121, 5813-5814.
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(1999)
J. Am. Chem. Soc
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-
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Vedejs, E.1
Daugulis, O.2
|