Taxane synthesis through intramolecular pinacol coupling at C-1 - C-2. Highly oxygenated C-aromatic taxanes

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 1109-1118

  Swindell, Charles S ^a   Fan, Weiming ^a  

^a BRYN MAWR COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030024340     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9519367     Document Type: Article

References (32)

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2. Isolation: (a) Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327. Synthesis: (b) Holton, R. A.; et al. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (c) Nicolaou, K. C ; et al. J. Am. Chem. Soc. 1995, 117, 624-633, 634-644, 645-652, 653-659. Recent reviews: (d) Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.: Springer-Verlag: Vienna, 1993; Vol. 61, pp 1-206. (e) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44. (f) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 1, 47-75.
3. Isolation: (a) Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327. Synthesis: (b) Holton, R. A.; et al. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (c) Nicolaou, K. C ; et al. J. Am. Chem. Soc. 1995, 117, 624-633, 634-644, 645-652, 653-659. Recent reviews: (d) Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.: Springer-Verlag: Vienna, 1993; Vol. 61, pp 1-206. (e) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44. (f) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 1, 47-75.
4. Isolation: (a) Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327. Synthesis: (b) Holton, R. A.; et al. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (c) Nicolaou, K. C ; et al. J. Am. Chem. Soc. 1995, 117, 624-633, 634-644, 645-652, 653-659. Recent reviews: (d) Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.: Springer-Verlag: Vienna, 1993; Vol. 61, pp 1-206. (e) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44. (f) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 1, 47-75.
5. Isolation: (a) Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327. Synthesis: (b) Holton, R. A.; et al. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (c) Nicolaou, K. C ; et al. J. Am. Chem. Soc. 1995, 117, 624-633, 634-644, 645-652, 653-659. Recent reviews: (d) Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.: Springer-Verlag: Vienna, 1993; Vol. 61, pp 1-206. (e) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44. (f) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 1, 47-75.
6. Isolation: (a) Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327. Synthesis: (b) Holton, R. A.; et al. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (c) Nicolaou, K. C ; et al. J. Am. Chem. Soc. 1995, 117, 624-633, 634-644, 645-652, 653-659. Recent reviews: (d) Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.: Springer-Verlag: Vienna, 1993; Vol. 61, pp 1-206. (e) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44. (f) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 1, 47-75.
7. Isolation: (a) Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327. Synthesis: (b) Holton, R. A.; et al. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (c) Nicolaou, K. C ; et al. J. Am. Chem. Soc. 1995, 117, 624-633, 634-644, 645-652, 653-659. Recent reviews: (d) Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.: Springer-Verlag: Vienna, 1993; Vol. 61, pp 1-206. (e) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15-44. (f) Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. Contemp. Org. Synth. 1994, 1, 47-75.
8. For a preliminary report of part of this work, see: Swindell, C. S.; Fan, W.; Klimko, P. G. Tetrahedron Lett. 1994, 35, 4959-4962.
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19. For a counterexample, see ref 2c.
20. Likewise with the corresponding oxygen acetal, we observed the following: (Matrix Presented)
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24. For another solution, see: Young, W. B.; Link, J. T., Masters, J. J.; Snyder, L. B.; Danishefsky, S. J.; De Gala, S. Tetrahedron Lett. 1995, 36, 4963-4966.
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26. See also: (b) Shea, K. J.; Gilman, J. W. J. Am. Chem. Soc. 1985, 107, 4791-4792. (c) Bonnert, R. V.; Jenkins, P. R. J. Chem. Soc., Perkin Trans. 1 1989, 413-418. (d) For a related Diels-Alder cycloaddition, see: Winkler, J. D.; Kim, H. S.; Kim, S. H. Tetrahedron Lett. 1995, 36, 687-690.
27. See also: (b) Shea, K. J.; Gilman, J. W. J. Am. Chem. Soc. 1985, 107, 4791-4792. (c) Bonnert, R. V.; Jenkins, P. R. J. Chem. Soc., Perkin Trans. 1 1989, 413-418. (d) For a related Diels-Alder cycloaddition, see: Winkler, J. D.; Kim, H. S.; Kim, S. H. Tetrahedron Lett. 1995, 36, 687-690.
28. See also: (b) Shea, K. J.; Gilman, J. W. J. Am. Chem. Soc. 1985, 107, 4791-4792. (c) Bonnert, R. V.; Jenkins, P. R. J. Chem. Soc., Perkin Trans. 1 1989, 413-418. (d) For a related Diels-Alder cycloaddition, see: Winkler, J. D.; Kim, H. S.; Kim, S. H. Tetrahedron Lett. 1995, 36, 687-690.
29. Seto, M.; Morihira, K.; Horiguchi, Y.; Kuwajima, I. J. Org. Chem. 1994, 59, 3165-3174.
30. (a) Wender, P. A.; et al. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; ACS Symp. Series 583; American Chemical Society; Washington, DC, 1995; Chapter 24.
31. (b) Wender, P. A.; Glass, T. E.; Krauss, N. E.; Mühlebach, M.; Peschke, B.; Rawlins, D. B Abstracts of Papers, 209th National Meeting of the American Chemical Society, Anaheim, CA; American Chemical Society: Washington, DC, 1995; ORGN 210.
32. For general features, see the preceding article (ref 1).