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15. For use in natural product synthesis, see: Martin, S. F.; Zinke, P. W. J. Org. Chem., 1991, 56, 6600-6606; DeShong, P.; Simpson, D. M.; Lin, M.-T. Tetrahedron Lett., 1989, 30, 2885-2888; DeShong, P.; Waltermire, R. E.; Ammon, H. L. J. Am. Chem. Soc., 1988, 110, 1901-1910; Brown, R. C. D.; Kocienski, P. J. Synlett, 1994, 417-419; Martin, S. F.; Lee, W.-C.; Pacofsky, G. J.; Gist, R. P.; Mulhern, R. A. J. Am. Chem. Soc., 1994, 116, 4674-4688.
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15. For use in natural product synthesis, see: Martin, S. F.; Zinke, P. W. J. Org. Chem., 1991, 56, 6600-6606; DeShong, P.; Simpson, D. M.; Lin, M.-T. Tetrahedron Lett., 1989, 30, 2885-2888; DeShong, P.; Waltermire, R. E.; Ammon, H. L. J. Am. Chem. Soc., 1988, 110, 1901-1910; Brown, R. C. D.; Kocienski, P. J. Synlett, 1994, 417-419; Martin, S. F.; Lee, W.-C.; Pacofsky, G. J.; Gist, R. P.; Mulhern, R. A. J. Am. Chem. Soc., 1994, 116, 4674-4688.
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15. For use in natural product synthesis, see: Martin, S. F.; Zinke, P. W. J. Org. Chem., 1991, 56, 6600-6606; DeShong, P.; Simpson, D. M.; Lin, M.-T. Tetrahedron Lett., 1989, 30, 2885-2888; DeShong, P.; Waltermire, R. E.; Ammon, H. L. J. Am. Chem. Soc., 1988, 110, 1901-1910; Brown, R. C. D.; Kocienski, P. J. Synlett, 1994, 417-419; Martin, S. F.; Lee, W.-C.; Pacofsky, G. J.; Gist, R. P.; Mulhern, R. A. J. Am. Chem. Soc., 1994, 116, 4674-4688.
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15. For use in natural product synthesis, see: Martin, S. F.; Zinke, P. W. J. Org. Chem., 1991, 56, 6600-6606; DeShong, P.; Simpson, D. M.; Lin, M.-T. Tetrahedron Lett., 1989, 30, 2885-2888; DeShong, P.; Waltermire, R. E.; Ammon, H. L. J. Am. Chem. Soc., 1988, 110, 1901-1910; Brown, R. C. D.; Kocienski, P. J. Synlett, 1994, 417-419; Martin, S. F.; Lee, W.-C.; Pacofsky, G. J.; Gist, R. P.; Mulhern, R. A. J. Am. Chem. Soc., 1994, 116, 4674-4688.
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16. For the reduction of a similar enone, see: Kametani, T.; Tsubuki, M.; Honda, T. Chem. Pharm. Bull., 1988, 36, 3706-3709.
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24
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0010547934
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note
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17. For the reductions of α-hydroxy ketones with borohydride reagents, see references 16 and 18.
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25
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19. Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett., 1968, 2199-2202; Anh, N. T. Top. Curr. Chem., 1980, 88, 145-162.
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29
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21. Collington, E. W.; Knight, J. G.; Wallis, C. J.; Warren, S. Tetrahedron Lett., 1989, 30, 877-880; Brown, K. M.; Lawrence, N. J.; Liddle, J.; Muhammad, F.; Jackson, D. A. Tetrahedron Lett., 1994, 35, 6733-6736; Vedejs, E.; Campbell, J. B.; Gadwood, R. C.; Rodgers, J. G.; Spear, K. L.; Watanabe, Y. J. Org. Chem., 1982, 47, 1534-1546; Clough, J. M.; Pattenden, G. Tetrahedron Lett., 1978, 4159-4162; Lythgoe, B. Chem. Rev., 1980, 80, 449-475.
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21. Collington, E. W.; Knight, J. G.; Wallis, C. J.; Warren, S. Tetrahedron Lett., 1989, 30, 877-880; Brown, K. M.; Lawrence, N. J.; Liddle, J.; Muhammad, F.; Jackson, D. A. Tetrahedron Lett., 1994, 35, 6733-6736; Vedejs, E.; Campbell, J. B.; Gadwood, R. C.; Rodgers, J. G.; Spear, K. L.; Watanabe, Y. J. Org. Chem., 1982, 47, 1534-1546; Clough, J. M.; Pattenden, G. Tetrahedron Lett., 1978, 4159-4162; Lythgoe, B. Chem. Rev., 1980, 80, 449-475.
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21. Collington, E. W.; Knight, J. G.; Wallis, C. J.; Warren, S. Tetrahedron Lett., 1989, 30, 877-880; Brown, K. M.; Lawrence, N. J.; Liddle, J.; Muhammad, F.; Jackson, D. A. Tetrahedron Lett., 1994, 35, 6733-6736; Vedejs, E.; Campbell, J. B.; Gadwood, R. C.; Rodgers, J. G.; Spear, K. L.; Watanabe, Y. J. Org. Chem., 1982, 47, 1534-1546; Clough, J. M.; Pattenden, G. Tetrahedron Lett., 1978, 4159-4162; Lythgoe, B. Chem. Rev., 1980, 80, 449-475.
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21. Collington, E. W.; Knight, J. G.; Wallis, C. J.; Warren, S. Tetrahedron Lett., 1989, 30, 877-880; Brown, K. M.; Lawrence, N. J.; Liddle, J.; Muhammad, F.; Jackson, D. A. Tetrahedron Lett., 1994, 35, 6733-6736; Vedejs, E.; Campbell, J. B.; Gadwood, R. C.; Rodgers, J. G.; Spear, K. L.; Watanabe, Y. J. Org. Chem., 1982, 47, 1534-1546; Clough, J. M.; Pattenden, G. Tetrahedron Lett., 1978, 4159-4162; Lythgoe, B. Chem. Rev., 1980, 80, 449-475.
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21. Collington, E. W.; Knight, J. G.; Wallis, C. J.; Warren, S. Tetrahedron Lett., 1989, 30, 877-880; Brown, K. M.; Lawrence, N. J.; Liddle, J.; Muhammad, F.; Jackson, D. A. Tetrahedron Lett., 1994, 35, 6733-6736; Vedejs, E.; Campbell, J. B.; Gadwood, R. C.; Rodgers, J. G.; Spear, K. L.; Watanabe, Y. J. Org. Chem., 1982, 47, 1534-1546; Clough, J. M.; Pattenden, G. Tetrahedron Lett., 1978, 4159-4162; Lythgoe, B. Chem. Rev., 1980, 80, 449-475.
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0010577823
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note
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2a
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-
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36
-
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0010547935
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note
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1,5syn-6 could be made from the same β-hydroxy phosphine oxide (4a) since 4c was itself synthesized from 4a by an oxidation-reduction sequence.
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37
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0030586137
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25. For other ways to analyse remote stereochemical relationships, see reference 28, references therein and: Neeland, E. G.; Sharadenda, A.; Weiler, L. Tetrahedron Lett., 1996, 37, 5069-5072; Stanway, S. J.; Thomas, E. J. J. Chem. Soc., Chem. Commun., 1994, 285-286.
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25. For other ways to analyse remote stereochemical relationships, see reference 28, references therein and: Neeland, E. G.; Sharadenda, A.; Weiler, L. Tetrahedron Lett., 1996, 37, 5069-5072; Stanway, S. J.; Thomas, E. J. J. Chem. Soc., Chem. Commun., 1994, 285-286.
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26. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc., 1991, 113, 4092-4096; Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc., 1973, 95, 512-519; Parker, D. Chem. Rev., 1991, 91, 1441-1457; Yamaguch, S. Asymmetric Synthesis, vol. 1, ch. 7, ed. Morrison, J. D., Academic Press, New York, 1983.
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26. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc., 1991, 113, 4092-4096; Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc., 1973, 95, 512-519; Parker, D. Chem. Rev., 1991, 91, 1441-1457; Yamaguch, S. Asymmetric Synthesis, vol. 1, ch. 7, ed. Morrison, J. D., Academic Press, New York, 1983.
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27. The absolute stereochemistry of similar allylic alcohols has been determined using Mosher's method: Pehk, T.; Lippma, E.; Lopp, M.; Paju, A.; Borer, B. C.; Taylor, R. J. K. Tetrahedron: Asymmetry, 1993, 4, 1527-1532.
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28. Thomas, E. J. J. Chem. Soc., Chem. Commun., 1997, 411-418; Carey, J. S.; Coulter, T. S.; Hallett, D. J.; Maguire, R. J.; McNeill, A. H.; Stanway, S. J.; Teerawutgulrag, A.; Thomas, E. J. Pure & App. Chem., 1996, 68, 707-710.
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Teerawutgulrag, A.7
Thomas, E.J.8
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