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1
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8544225999
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Also called Taxol, a registered trademark of the Bristol-Myers Squibb Company
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Also called Taxol, a registered trademark of the Bristol-Myers Squibb Company.
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2
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8544228854
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ACS Symposium Series 583; American Chemical Society: Washington, DC
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For general reviews on a variety of subjects in this area see: (a) Taxane Anticancer Agents; Georg, G. I., Chen, T. T., Ojima, I., Vyasi, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995. (b) Taxol: Science and Application; Suffness, M., Ed.; CRC: Boca Raton, 1995. (c) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44. (d) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 47.
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(1995)
Taxane Anticancer Agents
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Georg, G.I.1
Chen, T.T.2
Ojima, I.3
Vyasi, D.M.4
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3
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0003469887
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CRC: Boca Raton
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For general reviews on a variety of subjects in this area see: (a) Taxane Anticancer Agents; Georg, G. I., Chen, T. T., Ojima, I., Vyasi, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995. (b) Taxol: Science and Application; Suffness, M., Ed.; CRC: Boca Raton, 1995. (c) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44. (d) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 47.
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(1995)
Taxol: Science and Application
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Suffness, M.1
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4
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33748226949
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For general reviews on a variety of subjects in this area see: (a) Taxane Anticancer Agents; Georg, G. I., Chen, T. T., Ojima, I., Vyasi, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995. (b) Taxol: Science and Application; Suffness, M., Ed.; CRC: Boca Raton, 1995. (c) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44. (d) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 47.
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(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 15-44
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Nicolaou, K.C.1
Dai, W.-M.2
Guy, R.K.3
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5
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0004186924
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For general reviews on a variety of subjects in this area see: (a) Taxane Anticancer Agents; Georg, G. I., Chen, T. T., Ojima, I., Vyasi, D. M., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995. (b) Taxol: Science and Application; Suffness, M., Ed.; CRC: Boca Raton, 1995. (c) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44. (d) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 47.
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(1994)
Contemp. Org. Synth.
, pp. 47
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6
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0000052734
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Guenard, D.; Gueritte-Voegelein, F.; Potier, P. Acc. Chem. Res. 1993, 26, 160-167.
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(1993)
Acc. Chem. Res.
, vol.26
, pp. 160-167
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Guenard, D.1
Gueritte-Voegelein, F.2
Potier, P.3
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9
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8544234748
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Roberts, R. A.; Schüll, V.; Paquette, L. A. J. Org. Chem. 1983, 48, 2076-2084.
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(1983)
J. Org. Chem.
, vol.48
, pp. 2076-2084
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Roberts, R.A.1
Schüll, V.2
Paquette, L.A.3
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11
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0000024394
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Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047-1050.
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(1986)
Tetrahedron Lett.
, vol.27
, pp. 1047-1050
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Alexakis, A.1
Berlan, J.2
Besace, Y.3
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14
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0001520096
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Gololobov, Y. G.; Nesmeyanov, A. N.; Lysenko, V. P.; Boldeskul, I. E. Tetrahedron 1987, 43, 2609-2651.
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(1987)
Tetrahedron
, vol.43
, pp. 2609-2651
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Gololobov, Y.G.1
Nesmeyanov, A.N.2
Lysenko, V.P.3
Boldeskul, I.E.4
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15
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0028846802
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For recent examples, see: (a) Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014. (b) Thielemann, W.; Schafer, H. J.; Kotila, S. Tetrahedron 1995, 51, 12027-12034. (c) Kumar, P.; Rao, A. T.; Saravanan, K.; Pandey, B. Tetrahedron Lett. 1995, 36, 3397-3400. (d) Cossy, J.; Furet, N.; BouzBouz, S. Tetrahedron 1995, 51, 11751-11764. (e) Gustafsson, J.; Sterner, O. Tetrahedron 1995, 51, 3865-3872. (f) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220.
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(1995)
Tetrahedron
, vol.51
, pp. 13003-13014
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Schneider, M.F.1
Junga, H.2
Blechert, S.3
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16
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0028882955
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For recent examples, see: (a) Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014. (b) Thielemann, W.; Schafer, H. J.; Kotila, S. Tetrahedron 1995, 51, 12027-12034. (c) Kumar, P.; Rao, A. T.; Saravanan, K.; Pandey, B. Tetrahedron Lett. 1995, 36, 3397-3400. (d) Cossy, J.; Furet, N.; BouzBouz, S. Tetrahedron 1995, 51, 11751-11764. (e) Gustafsson, J.; Sterner, O. Tetrahedron 1995, 51, 3865-3872. (f) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220.
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(1995)
Tetrahedron
, vol.51
, pp. 12027-12034
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Thielemann, W.1
Schafer, H.J.2
Kotila, S.3
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17
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0028917355
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For recent examples, see: (a) Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014. (b) Thielemann, W.; Schafer, H. J.; Kotila, S. Tetrahedron 1995, 51, 12027-12034. (c) Kumar, P.; Rao, A. T.; Saravanan, K.; Pandey, B. Tetrahedron Lett. 1995, 36, 3397-3400. (d) Cossy, J.; Furet, N.; BouzBouz, S. Tetrahedron 1995, 51, 11751-11764. (e) Gustafsson, J.; Sterner, O. Tetrahedron 1995, 51, 3865-3872. (f) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 3397-3400
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Kumar, P.1
Rao, A.T.2
Saravanan, K.3
Pandey, B.4
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18
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0028884569
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For recent examples, see: (a) Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014. (b) Thielemann, W.; Schafer, H. J.; Kotila, S. Tetrahedron 1995, 51, 12027-12034. (c) Kumar, P.; Rao, A. T.; Saravanan, K.; Pandey, B. Tetrahedron Lett. 1995, 36, 3397-3400. (d) Cossy, J.; Furet, N.; BouzBouz, S. Tetrahedron 1995, 51, 11751-11764. (e) Gustafsson, J.; Sterner, O. Tetrahedron 1995, 51, 3865-3872. (f) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220.
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(1995)
Tetrahedron
, vol.51
, pp. 11751-11764
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Cossy, J.1
Furet, N.2
BouzBouz, S.3
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19
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0028968175
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For recent examples, see: (a) Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014. (b) Thielemann, W.; Schafer, H. J.; Kotila, S. Tetrahedron 1995, 51, 12027-12034. (c) Kumar, P.; Rao, A. T.; Saravanan, K.; Pandey, B. Tetrahedron Lett. 1995, 36, 3397-3400. (d) Cossy, J.; Furet, N.; BouzBouz, S. Tetrahedron 1995, 51, 11751-11764. (e) Gustafsson, J.; Sterner, O. Tetrahedron 1995, 51, 3865-3872. (f) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220.
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(1995)
Tetrahedron
, vol.51
, pp. 3865-3872
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Gustafsson, J.1
Sterner, O.2
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20
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0028141792
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For recent examples, see: (a) Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014. (b) Thielemann, W.; Schafer, H. J.; Kotila, S. Tetrahedron 1995, 51, 12027-12034. (c) Kumar, P.; Rao, A. T.; Saravanan, K.; Pandey, B. Tetrahedron Lett. 1995, 36, 3397-3400. (d) Cossy, J.; Furet, N.; BouzBouz, S. Tetrahedron 1995, 51, 11751-11764. (e) Gustafsson, J.; Sterner, O. Tetrahedron 1995, 51, 3865-3872. (f) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217-7220.
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(1994)
Tetrahedron Lett.
, vol.35
, pp. 7217-7220
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Kirschberg, T.1
Mattay, J.2
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21
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0001367505
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For typical examples, see: (a) Yankee, E. W.; Badea, F. D.; Howe, N. E.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 4210-4219. (b) Kaiser, C.; Trost, B. M.; Beeson, J.; Weinstock, J. J. Org. Chem. 1965, 30, 3972-3975. (c) Annen, K.; Hofmeister, H.; Laurent, H.; Seeger, A.; Wiechert, R. Chem. Ber. 1978, 111, 3094-3104.
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(1973)
J. Am. Chem. Soc.
, vol.95
, pp. 4210-4219
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Yankee, E.W.1
Badea, F.D.2
Howe, N.E.3
Cram, D.J.4
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22
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0011394814
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For typical examples, see: (a) Yankee, E. W.; Badea, F. D.; Howe, N. E.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 4210-4219. (b) Kaiser, C.; Trost, B. M.; Beeson, J.; Weinstock, J. J. Org. Chem. 1965, 30, 3972-3975. (c) Annen, K.; Hofmeister, H.; Laurent, H.; Seeger, A.; Wiechert, R. Chem. Ber. 1978, 111, 3094-3104.
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(1965)
J. Org. Chem.
, vol.30
, pp. 3972-3975
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Kaiser, C.1
Trost, B.M.2
Beeson, J.3
Weinstock, J.4
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23
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0008750085
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For typical examples, see: (a) Yankee, E. W.; Badea, F. D.; Howe, N. E.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 4210-4219. (b) Kaiser, C.; Trost, B. M.; Beeson, J.; Weinstock, J. J. Org. Chem. 1965, 30, 3972-3975. (c) Annen, K.; Hofmeister, H.; Laurent, H.; Seeger, A.; Wiechert, R. Chem. Ber. 1978, 111, 3094-3104.
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(1978)
Chem. Ber.
, vol.111
, pp. 3094-3104
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Annen, K.1
Hofmeister, H.2
Laurent, H.3
Seeger, A.4
Wiechert, R.5
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25
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0002133684
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Minami, T.; Matsumoto, M.; Suganuma, H.; Agawa, T. J. Org. Chem. 1978, 43, 2149-2153.
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(1978)
J. Org. Chem.
, vol.43
, pp. 2149-2153
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Minami, T.1
Matsumoto, M.2
Suganuma, H.3
Agawa, T.4
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26
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8544239898
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note
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We believe that this modest isolated yield is a function of the product isolation efficiency.
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27
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8544275598
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note
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2 (1.2 equiv), 50°C, 12 h. GC analysis showed 21% conversion to product 13 in both cases.
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29
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8544264355
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note
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2, Pd/C, or Raney nickel. Temperatures as high as 60°C and hydrogen pressures as high as 1500 psi were employed.
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32
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0026476016
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Srikrishna, A.; Krishnan, K.; Yelamagged, C. V. Tetrahedron 1992, 48, 9725-9734.
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(1992)
Tetrahedron
, vol.48
, pp. 9725-9734
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Srikrishna, A.1
Krishnan, K.2
Yelamagged, C.V.3
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33
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8544266554
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note
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In retrospect, it is not surprising that the lactone functionality was reduced. Treatment of β-keto ester i with lithium in liquid ammonia is known to afford hydrindanone ii and decalin iii, where cyclopropane reduction is accompanied by reduction of the ester group (ref 21). (Matrix Presented)
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35
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0000075150
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(b) Swindell, C. S.; Patel, B. P.; deSolms, S. J.; Springer J. P. J. Org. Chem. 1987, 52, 2346-2355.
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(1987)
J. Org. Chem.
, vol.52
, pp. 2346-2355
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Swindell, C.S.1
Patel, B.P.2
Desolms, S.J.3
Springer, J.P.4
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37
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84986409793
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(d) Neh, H.; Kühling, A.; Blechert, S. Helv. Chim. Acta 1989, 72, 101-109.
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(1989)
Helv. Chim. Acta
, vol.72
, pp. 101-109
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Neh, H.1
Kühling, A.2
Blechert, S.3
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38
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8544248432
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Rahman, A. U., Ed.; Elsevier Science: New York
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(e) Paquette, L. A. In Studies in Natural Products Chemistry; Rahman, A. U., Ed.; Elsevier Science: New York, 1992; Vol. 11, pp 52-54.
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(1992)
Studies in Natural Products Chemistry
, vol.11
, pp. 52-54
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Paquette, L.A.1
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41
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0002714675
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Still, W. C.; Khan, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
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(1978)
J. Org. Chem.
, vol.43
, pp. 2923-2925
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Still, W.C.1
Khan, M.2
Mitra, A.3
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42
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8544275038
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note
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This resonance was not reported in reference 5; instead, a signal at δ 150.0 was cited.
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43
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8544247697
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note
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2 carbon resonance was not observable above the spectral base line.
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