Total Synthesis of (−)-Colchicine by an Oxyallyl [4+3] Cycloaddition

Author:

Lee Jae Chol,Cha Jin Kun

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference26 articles.

1. Part 12 in the series of synthetic studies on [4+3] cycloadditions of oxyallyls. See also: (a) Part 11: Sung, M. J.; Lee, H. I.; Chong, Y.; Cha, J. K. Org. Lett. in press. (b) Part 10: Lee, K.; Cha, J. K. Org. Lett. 1999, 1, 523. (b) Part 9: Cho, S. Y.; Lee, J. C.; Cha, J. K. J. Org. Chem. 1999, 64, 3394.

2. For general reviews of 1, see: (a) Wildman, W. C.; Pursey, B. A. The Alkaloids 1968, 11, 407. (b) Capraro, H.-G.; Brossi, A. The Alkaloids 1984, 23, 1. (c) Boyé, O; Brossi, A. The Alkaloids 1992, 41, 125. (d) Le Hello, C. The Alkaloids 2000, 53, 287.

3. For a general review of 4–6, see: (a) Buck, K. T. The Alkaloids 1984, 23, 301. For successful total syntheses, see: (b) Banwell, M. G.; Hamel, E.; Ireland, N. K.; Mackay, M. F. Heterocycles 1994, 39, 205. (c) Banwell, M. G.; Ireland, N. K. J. Chem. Soc., Chem. Commun. 1994, 591. (d) Boger, D. L.; Takahashi, K. J. Am. Chem. Soc. 1995, 117, 12452.

4. (a) Wolff, J.; Capraro, H.-G.; Brossi, A.; Cook, G. H. J. Biol. Chem. 1980, 255, 7144. (b) Berg, U.; Deinum, J.; Lincoln, P.; Kvassman, J. Bioorg. Chem. 1991, 19, 53.

5. (a) Schreiber, J.; Leimgruber, W.; Pesaro, M.; Schudel, P.; Threlfall, T.; Eschenmoser, A. Helv. Chim. Acta 1961, 44, 540. (b) van Tamelen, E. E.; Spencer, T. A.; Allen, D. S.; Orvis, R. L. Tetrahedron 1961, 14, 8. (c) Scott, A. I.; McCapra, F.; Buchanan, R. L.; Day, A. C.; Young, D. W. Tetrahedron 1965, 21, 3605. (d) Martel, J.; Toromanoff, E.; Huynh, C. J. Org. Chem. 1965, 30, 1752. (e) Kato, M.; Kido, F.; Wu, M. D.; Yoshikoshi, A. Bull. Chem. Soc. Jpn 1974, 47, 1516. (f) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6713 and references therein.

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