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For recent examples, see: (a) Suga, S.; Watanabe, M.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 14824. (b) Koseki, Y.; Sato, H.; Watanabe, Y.; Nagasaka, T. Org. Lett. 2002, 4, 885. (c) Tietze, L. F.; Schirok, H. J. Am. Chem. Soc. 1999, 121, 10264.
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For recent examples, see: (a) Suga, S.; Watanabe, M.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 14824. (b) Koseki, Y.; Sato, H.; Watanabe, Y.; Nagasaka, T. Org. Lett. 2002, 4, 885. (c) Tietze, L. F.; Schirok, H. J. Am. Chem. Soc. 1999, 121, 10264.
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For recent examples, see: (a) Worden, S. M.; Mapitse, R.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6011. (b) Booker-Milburn, K. I.; Dudin, L. F.; Anson, C. E.; Guile, S. D. Org. Lett. 2001, 3, 3005. (c) Kim, S.-H.; Cha, J. K. Synthesis 2000, 2113. (d) Beall, L. S.; Padwa, A. Tetrahedron Lett. 1998, 39, 4159. (e) Molander, G. A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347. (f) De Oliveira, E. R.; Dumas, F.; D'Angelo, J. Tetrahedron Lett. 1997, 38, 3723.
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For recent examples, see: (a) Worden, S. M.; Mapitse, R.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6011. (b) Booker-Milburn, K. I.; Dudin, L. F.; Anson, C. E.; Guile, S. D. Org. Lett. 2001, 3, 3005. (c) Kim, S.-H.; Cha, J. K. Synthesis 2000, 2113. (d) Beall, L. S.; Padwa, A. Tetrahedron Lett. 1998, 39, 4159. (e) Molander, G. A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347. (f) De Oliveira, E. R.; Dumas, F.; D'Angelo, J. Tetrahedron Lett. 1997, 38, 3723.
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For recent examples, see: (a) Worden, S. M.; Mapitse, R.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6011. (b) Booker-Milburn, K. I.; Dudin, L. F.; Anson, C. E.; Guile, S. D. Org. Lett. 2001, 3, 3005. (c) Kim, S.-H.; Cha, J. K. Synthesis 2000, 2113. (d) Beall, L. S.; Padwa, A. Tetrahedron Lett. 1998, 39, 4159. (e) Molander, G. A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347. (f) De Oliveira, E. R.; Dumas, F.; D'Angelo, J. Tetrahedron Lett. 1997, 38, 3723.
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Kim, S.-H.1
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For recent examples, see: (a) Worden, S. M.; Mapitse, R.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6011. (b) Booker-Milburn, K. I.; Dudin, L. F.; Anson, C. E.; Guile, S. D. Org. Lett. 2001, 3, 3005. (c) Kim, S.-H.; Cha, J. K. Synthesis 2000, 2113. (d) Beall, L. S.; Padwa, A. Tetrahedron Lett. 1998, 39, 4159. (e) Molander, G. A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347. (f) De Oliveira, E. R.; Dumas, F.; D'Angelo, J. Tetrahedron Lett. 1997, 38, 3723.
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For recent examples, see: (a) Worden, S. M.; Mapitse, R.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6011. (b) Booker-Milburn, K. I.; Dudin, L. F.; Anson, C. E.; Guile, S. D. Org. Lett. 2001, 3, 3005. (c) Kim, S.-H.; Cha, J. K. Synthesis 2000, 2113. (d) Beall, L. S.; Padwa, A. Tetrahedron Lett. 1998, 39, 4159. (e) Molander, G. A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347. (f) De Oliveira, E. R.; Dumas, F.; D'Angelo, J. Tetrahedron Lett. 1997, 38, 3723.
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For recent examples, see: (a) Worden, S. M.; Mapitse, R.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6011. (b) Booker-Milburn, K. I.; Dudin, L. F.; Anson, C. E.; Guile, S. D. Org. Lett. 2001, 3, 3005. (c) Kim, S.-H.; Cha, J. K. Synthesis 2000, 2113. (d) Beall, L. S.; Padwa, A. Tetrahedron Lett. 1998, 39, 4159. (e) Molander, G. A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347. (f) De Oliveira, E. R.; Dumas, F.; D'Angelo, J. Tetrahedron Lett. 1997, 38, 3723.
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0141623696
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note
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See the Supporting Information for details.
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21
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0141623692
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note
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tBu in THF or DMF resulted in a low and irreproducible yield of 9.
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22
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0000080952
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Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
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0141512474
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note
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The putative pentacyclic ketone 2 had not been actually synthesized prior to this work; cf. refs 1b and 6.
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24
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0141623695
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note
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We thank Professor Xiao-Tian Liang of Beijing Institute of Materia Medica for a gift of natural cephalotaxine.
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33
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0141735566
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Studies along this line toward natural product synthesis are in progress and will be reported in due course.
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For leading references, see: (a) Leonard, N. J.; Hay, A. S.; Fulmer, R. W.; Gash, V. W. J. Am. Chem. Soc. 1955, 77, 439. (b) Leonard, N. J.; Fulmer, R. W.; Hay, A. S. J. Am. Chem. Soc. 1956, 78, 3457.
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0141623693
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6a that, on treatment of keto enamine 16 with a hot mixture of HOAc-NaOAc, the formation of a new product with practically identical IR maxima absorptions with that of 17, but did not further characterize its structure.
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For attempted biomimetic synthesis, see: (a) Marino, J. P.; Samanen, J. M. J. Org. Chem. 1976, 41, 179. (b) Kupchan, S. M.; Dhingra, O. P.; Kim, C.-K. J. Org. Chem. 1978, 43, 4464.
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For attempted biomimetic synthesis, see: (a) Marino, J. P.; Samanen, J. M. J. Org. Chem. 1976, 41, 179. (b) Kupchan, S. M.; Dhingra, O. P.; Kim, C.-K. J. Org. Chem. 1978, 43, 4464.
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|