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Denis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S.; Greene, A. E. J. Chem Soc., Perkin Trans. I 1995, 1811-1815. See also: Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem Soc., Perkin Trans. 1 1996, 2869-2872. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666. Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
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Mantellier, P.5
Jost, S.6
Greene, A.E.7
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0242617763
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Denis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S.; Greene, A. E. J. Chem Soc., Perkin Trans. I 1995, 1811-1815. See also: Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem Soc., Perkin Trans. 1 1996, 2869-2872. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666. Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
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Génisson, Y.1
Massardier, C.2
Gautier-Luneau, I.3
Greene, A.E.4
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16044369708
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Denis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S.; Greene, A. E. J. Chem Soc., Perkin Trans. I 1995, 1811-1815. See also: Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem Soc., Perkin Trans. 1 1996, 2869-2872. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666. Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
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Kant, J.1
Schwartz, W.S.2
Fairchild, C.3
Gao, Q.4
Huang, S.5
Long, B.H.6
Kadow, J.F.7
Farina, V.8
Vyas, D.9
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11
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0032575139
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Denis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S.; Greene, A. E. J. Chem Soc., Perkin Trans. I 1995, 1811-1815. See also: Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem Soc., Perkin Trans. 1 1996, 2869-2872. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666. Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
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Ojima, I.1
Wang, T.2
Delaloge, F.3
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12
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0032563850
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Denis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S.; Greene, A. E. J. Chem Soc., Perkin Trans. I 1995, 1811-1815. See also: Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem Soc., Perkin Trans. 1 1996, 2869-2872. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666. Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
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Barboni, L.1
Lambertucci, C.2
Ballini, R.3
Appendino, G.4
Bombardelli, E.5
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13
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12244289216
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note
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In view of the large number of diverse taxol and taxotere derivatives published to date, it is surprising that this is apparently the first example of substitution at C-3′.
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14
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0002674759
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Georg, G. I., Ed.; VCH Publishers: New York
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(a) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; pp 295-368.
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Georg, G.I.1
Ravikumar, V.T.2
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15
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8244235132
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(b) Palomo, C.; Aizpurua, J. M.; Garcia, J. M.; Galarza, R.; Legido, M.; Urchegui, R.; Román, P.; Luque, A.; Server-Carrió, J.; Linden, A. J. Org. Chem. 1997, 62, 2070-2079.
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Aizpurua, J.M.2
Garcia, J.M.3
Galarza, R.4
Legido, M.5
Urchegui, R.6
Román, P.7
Luque, A.8
Server-Carrió, J.9
Linden, A.10
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16
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0032707721
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(c) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223-3235.
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Palomo, C.1
Aizpurua, J.M.2
Gamboa, I.3
Oiarbide, M.4
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17
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0001521888
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For general reviews on asymmetric methods to create quaternary centers and use of these methods in natural product synthesis, see: Fuji, K. Chem. Rev. 1993, 93, 2037-2066. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401 and references therein.
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Chem. Rev.
, vol.93
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Fuji, K.1
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18
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0032473509
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and references therein
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For general reviews on asymmetric methods to create quaternary centers and use of these methods in natural product synthesis, see: Fuji, K. Chem. Rev. 1993, 93, 2037-2066. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401 and references therein.
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Angew. Chem., Int. Ed.
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Corey, E.J.1
Guzman-Perez, A.2
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20
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0032554963
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(a) Brown, S.; Jordan, A. M.; Lawrence, N. J.; Pritchard, R. G.; McGown, A. T. Tetrahedron Lett.1998, 39, 3559-3562.
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Tetrahedron Lett.
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Brown, S.1
Jordan, A.M.2
Lawrence, N.J.3
Pritchard, R.G.4
McGown, A.T.5
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21
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0035544073
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(b) See also: Bull, S. D.; Davies, S. G.; Kelly, P. M.; Gianotti, M.; Smith, A. D. J. Chem Soc., Perkin Trans. 1 2001, 3106-3111.
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J. Chem Soc., Perkin Trans. 1
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Bull, S.D.1
Davies, S.G.2
Kelly, P.M.3
Gianotti, M.4
Smith, A.D.5
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22
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12244292625
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Lancaster Synthesis, Bischheim-Strasbourg, France
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Lancaster Synthesis, Bischheim-Strasbourg, France.
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23
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12244267636
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note
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Our earlier efforts with 1-phenylethylamine and 1-(2,6-dichlorophenyl)ethylamine were unsuccessful: the β-lactam resulting from the former could not be cleanly freed of the α-methylbenzyl group and the acetophenone imine derived from the latter proved a poor ketene partner in the Staudinger reaction.
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25
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12244256715
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note
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For comparison, the imine from benzaldehyde and 1-phenylethylamine with acetoxyacetyl chloride has been reported to give diastereomeric ratios of 60:40 and 75:25 (60 and 74% yields).
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26
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0000344501
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See also ref 4a,c
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For a recent discussion of the stereochemical outcome of the Staudinger reaction, see: Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869-5876. See also ref 4a,c.
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(1998)
J. Org. Chem.
, vol.63
, pp. 5869-5876
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Arrieta, A.1
Lecea, B.2
Cossio, F.P.3
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27
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12244285602
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note
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In THF, the ratio was higher, but the yield was considerably lower (83:17, 43%). Solvent effects on the ratio of diastereomers in the Staudinger reaction have previous been noted. See, for example, ref 7a.
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28
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12244259651
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note
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3, F(000) = 752, θ range 2.10-72°, 2229 measured reflections, 2229 independent reflections, R(1) [I > 1.5σ] = 0.044, wR2 [all data] = 0.0468, GoF (all data) = 1.887.
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29
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12244272363
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note
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3, F(000) = 332, θ range 2.63-30° 10 043 measured reflections, 4544 [R(int) = 0.09] independent reflections, R(1) [I > 3σ] = 0.0496, wR2 [all data] = 0.0664, GoF (all data) = 1.903.
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30
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12244270306
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Sénilh, V.; Guéritte, F.; Guénard, D.; Colin, M.; Potier, P. C. R. Seances Acad. Sci., Ser. 2 1981, 293, 501-503 (troc = 2,2,2-trichloroethoxycarbonyl).
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(1981)
C.R. Seances Acad. Sci., Ser. 2
, vol.293
, pp. 501-503
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Sénilh, V.1
Guéritte, F.2
Guénard, D.3
Colin, M.4
Potier, P.5
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31
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0027173282
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Ojima, I.; Sun, C. M.; Zucco, M.; Park, Y. H.; Duclos, O.; Kuduk, S. Tetrahedron Lett. 1993, 34, 4149-4152.
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(1993)
Tetrahedron Lett.
, vol.34
, pp. 4149-4152
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Ojima, I.1
Sun, C.M.2
Zucco, M.3
Park, Y.H.4
Duclos, O.5
Kuduk, S.6
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