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Yamada, K.1
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Arakawa, M.6
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2
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0028133332
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Kigoshi, H.1
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Sakakura, A.6
Ogawa, T.7
Yamada, K.8
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3
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16044370146
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(b) Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.: Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5326.
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Kigoshi, H.1
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Ishiwata, H.6
Sakakura, A.7
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4
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0029066587
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(c) Suenaga, K.; Ishigaki, T.; Sakakura, A.; Kigoshi, H.; Yamada, K. Tetrahedron Lett. 1995, 36, 5053.
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Suenaga, K.1
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6
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0032514419
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4. Paterson, I.; Woodrow, M. D.; Cowden, C. J. Tetrahedron Lett. 1998, 38, 6041.
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Paterson, I.1
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5. (a) Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedron Lett. 1989, 30, 7121.
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(b) Paterson, I.; Norcross, R. D.; Ward, R. A.; Romca, P.; Lister, M. A. J. Am. Chem. Soc. 1994, 116, 11287.
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Lister, M.A.5
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10
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0010486888
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note
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6. Ketone (R)-8 was prepared in 3 steps from methyl (R)-3-hydroxy-2-methylpropionate with the PMB protecting group introduced using PMBC(=NH)CCl3/TIOH (ref. 5, 19).
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12
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0000783814
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(b) Kita, Y.; Okunaka, R.; Honda, T.; Shindo, M.; Taniguchi, M.; Kondo, M.; Sasho, M. J. Org. Chem. 1991, 56, 119.
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Kita, Y.1
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Shindo, M.4
Taniguchi, M.5
Kondo, M.6
Sasho, M.7
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13
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0010486889
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note
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13C NMR δ (62.9 MHz, CDCl3) 202.8, 132.6, 131.6, 80.3, 76.7, 76.6, 63.6, 55.6, 50.9, 42.7, 39.0, 38.8, 34.1, 27.5, 27.3, 24.8, 21.6, 20.9, 20.4, 18.1, 15.2, 13.8, 11.9.
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15
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0010450669
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note
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7.
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17
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73349127924
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(b) Trost, B. M.; Kazmaier, U. J. Am. Chem. Soc. 1992, 114, 7933. See also Kazmaier, U. Tetrahedron 1998, 54, 1491.
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Trost, B.M.1
Kazmaier, U.2
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18
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0032546058
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(b) Trost, B. M.; Kazmaier, U. J. Am. Chem. Soc. 1992, 114, 7933. See also Kazmaier, U. Tetrahedron 1998, 54, 1491.
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Kazmaier, U.1
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19
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0010450068
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note
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12. The PMP acetal configuration in 4 and 13 was assigned based upon the nOe's indicated for i. (formula presented)
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20
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0029619410
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Selective removal of a PMB ether in the presence of a PMP acetal has been reported previously. For example, see: In contrast, our initial route to the aplyronines was revised because of the inability to deprotect the PMB ether in ii without reaction at the PMP acetal
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13. Selective removal of a PMB ether in the presence of a PMP acetal has been reported previously. For example, see: Smith, A. B. III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. In contrast, our initial route to the aplyronines was revised because of the inability to deprotect the PMB ether in ii without reaction at the PMP acetal.
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Smith A.B. III1
Qiu, Y.2
Jones, D.R.3
Kobayashi, K.4
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23
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33845278140
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16. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
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Evans, D.A.1
Chapman, K.T.2
Carreira, E.M.3
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25
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0020609216
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18. Herold, P.; Mohr, P.; Tamm, C. Helv. Chim. Acta 1983, 66, 744.
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Herold, P.1
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Tamm, C.3
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26
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0001759396
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19. Nakajima, N., Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139.
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Nakajima, N.1
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Yonemitsu, O.4
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29
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33845282438
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22. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
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Corey, E.J.1
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Singh, V.K.5
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30
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0026035110
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(b) Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Jones, E. T. T.; Reamer, R. A.; Roberts, F. E.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 763.
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Jones, T.K.1
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Jones, E.T.T.7
Reamer, R.A.8
Roberts, F.E.9
Grabowski, E.J.J.10
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31
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0025068753
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Use of the butyl oxazaborolidine and/or catecholborane as stoichiometric reductant did not improve the selectivity and lower yields resulted see Other asymmetric reducing agents such as those derived from LiA1H4 also proved unsatisfactory
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23. Use of the butyl oxazaborolidine and/or catecholborane as stoichiometric reductant did not improve the selectivity and lower yields resulted (see Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611). Other asymmetric reducing agents such as those derived from LiA1H4 also proved unsatisfactory.
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Corey, E.J.1
Bakshi, R.K.2
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2142858450
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24. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
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Ohtani, I.1
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Kakisawa, H.4
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33
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0028965619
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Precedent based on results in ref. 22(a) in conjunction with those of: (a)
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25. Precedent based on results in ref. 22(a) in conjunction with those of: (a) Bach, J.; Berenguer, R.; Garcia, J.; Vilarrasa, J. Tetrahedron 1995, 36, 3425.
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Bach, J.1
Berenguer, R.2
Garcia, J.3
Vilarrasa, J.4
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(b) Bach, J.; Berenguer, R.; Farràs, J.; Garcia, J.; Meseguer, J.; Vilarrasa, J. Tetrahedron: Assymmetry 1995, 6, 2683.
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Bach, J.1
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Vilarrasa, J.6
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35
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46149140781
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26. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021.
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Horita, K.1
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Yonemitsu, O.5
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