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For several recent general reviews, see: (a) Kingston, D. G. I.; Molinero, A. D.; Rinaldi, J. M. In Progress in the Chemistry of Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.; Springer-Verlag: Vienna, 1993; Vol. 61, pp 1-206.
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The total synthesis of paclitaxel has recently been achieved
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The total synthesis of paclitaxel has recently been achieved: (a) Holton, R.A.; et al. J Am. Chem. Soc. 1994, 116, 1597, 1599.
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For reviews dealing with the construction of the taxane A ring, see refs 1b,c,d. For other recent synthetic approaches to the taxane A ring, see
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For reviews dealing with the construction of the taxane A ring, see refs 1b,c,d. For other recent synthetic approaches to the taxane A ring, see: (a) Alcaraz, L.; Harnett, J. J.; Mioskowski, C.; LeGall, T.; Shin, D.-S.; Falck, J. R. J. Org. Chem. 1995, 60, 7209.
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(d) Magnus, P.; Booth, J.; Diorazio, L.; Donohoe, T.; Lynch, V.; Magnus, N.; Mendoza, J.; Pye, P; Tarrant, J. Tetrahedron 1996, 52, 14103.
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(f) Sonawane, H. R.; Sudrik, S. G.; Jakkam, M. M.; Ramani, A.; Chanda, B. Synlett 1996, 175.
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(i) Kerkar, B.; Dokhac, D.; Fetizon, M.; Guir, F. Tetrahedron Lett. 1997, 38, 3223.
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0009488011
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For Diels-Alder approaches to the taxane A ring using captodative dienophiles but where the C-1 oxygen is not directly established in the cycloaddition step, see
-
For Diels-Alder approaches to the taxane A ring using captodative dienophiles but where the C-1 oxygen is not directly established in the cycloaddition step, see: (a) Masamune, T.; Fukuzawa, A.; Furusaki, A.; Ikura, M.; Matsue, H.; Kaneko, T.; Abiko, A.; Sakamoto, N.; Tanimoto, N.; Murai, A. Bull. Chem. Soc. Jpn. 1987, 60, 1001.
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(b) Tjepkema, M. W.; Wilson, P. D.; Wong, T.; Romero, M. A.; Audrain, H.; Fallis, A. G. Tetrahedron Lett. 1995, 36, 6039.
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84892593092
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Also see ref. 2b, c
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(c) Also see ref. 2b, c.
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24
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0029889487
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After completion of most of the work described herein, Funk and Yost reported a related approach to that outlined in this paper; however they employed a 2-(acyloxy)acrolein rather than an α-(aroyloxy) enone as the captodative dienophile
-
After completion of most of the work described herein, Funk and Yost reported a related approach to that outlined in this paper; however they employed a 2-(acyloxy)acrolein rather than an α-(aroyloxy) enone as the captodative dienophile: Funk, R. L.; Yost, K. J., III. J. Org. Chem. 1996, 61, 2598.
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For other reports of the dimerization of diene 5, see
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0000131109
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For a review suggesting the use of alkyl aluminum species as both Lewis acids and proton scavengers, see
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For a review suggesting the use of alkyl aluminum species as both Lewis acids and proton scavengers, see: Snider, B. B.; Rodini, D. J.; Karras, M.; Kirk, T. C.; Deutsch, E. A.; Cordova, R.; Price, R. T. Tetrahedron 1981, 37, 3927.
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0000172509
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For an example of the use of molecular sieves in a Diels-Alder reaction, see
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For an example of the use of molecular sieves in a Diels-Alder reaction, see: (a) Ketter, A.; Glahsl, G.; Herrmann, R. J. Chem. Res. Synop. 1990, 278;
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J. Chem. Res. Miniprint 1990, 2118.
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37
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2,6 DtBP
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2,6 DtBP: Brown, H. C.; Kanner, B. J. Am. Chem. Soc. 1966, 88, 986.
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For other examples of the use of 2,6-DtBP as a proton scavenger in organic reactions, see
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For other examples of the use of 2,6-DtBP as a proton scavenger in organic reactions, see: (a) Stang, P. J.; Anderson, A. G. J. Am. Chem. Soc. 1978, 100, 1520.
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47
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84892614076
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note
-
The dienophile was precomplexed with the Lewis acid, and the following addition adducts were obtained in a 2:1 ratio: (Chemical Equation Presented)
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