Two-directional synthesis. Part 1: A short formal synthesis of (±)-histrionicotoxin and (±)-histrionicotoxin 235A

Author:

Stockman Robert A

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference12 articles.

1. (a) Witkop, B. Experientia 1971, 27, 1121. (b) Daly, J. W.; Karle, I.; Meyers, W.; Tokuyama, T.; Waters, J. A.; Witkop, B. Proc. Natl. Acad. Sci. USA 1971, 68, 1870. (c) Tokuyama, T.; Venoyama, K.; Brown, G.; Daly, J. W.; Witkop, B. Helv. Chim. Acta 1974, 57, 2597. (d) Karle, I. J. Am. Chem. Soc. 1973, 95, 4036.

2. (a) Rapier, C.; Wannacot, S.; Lunt, G. G.; Alberquerque, E. X. FEBS Lett. 1987, 212, 292. (b) Oliviera, L.; Madison, B. W.; Kapai, H.; Sherby, S. M.; Swanson, K. L.; Edelfraui, M. E.; Alberquerque, E. X. Eur. J. Pharmacol. 1987, 140, 331. (c) Sobel, A.; Heidmann, T.; Hofler, J.; Changeaux, J. P. Proc. Natl. Acad. Sci. USA 1978, 75, 510.

3. For reviews, see: (a) Kotera, M. Bull. Soc. Chim. Fr. 1989, 370. (b) Grössinger, E. In The Alkaloids; Brossi, A., Ed.; Academic: New York, 1983; pp. 139–251. (c) Inubushi, Y.; Ibuka, T. Heterocycles 1982, 17, 507.

4. For syntheses not covered by reviews, see: (a) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B. J. Am. Chem. Soc. 1999, 121, 4900. (b) Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875. (c) Luzzio, F. A.; Fitch, R. W. J. Org. Chem. 1999, 64, 5485. (d) Tanner, D.; Hagberg, L.; Poulsen, A. Tetrahedron 1999, 55, 1427. (e) Comins, D. L.; Zhang, Y.; Zheng, X. Chem. Commun. 1998, 2509. (f) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907. (g) Kim, D.; Hong, S. W.; Park, C. W. Chem. Commun. 1997, 2263. (h) Compain, P.; Gore, J.; Vatele, J. M. Tetrahedron Lett. 1995, 36, 4063. (i) Maezaki, N.; Fukuyama, H.; Yagi, S.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835. (j) Zhu, J.; Royer, J.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1991, 32, 2485. (k) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852. For synthetic approaches, see: (l) Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681. (m) Parsons, P. J.; Angell, R.; Naylor, A.; Tyrell, E. J. Chem. Soc., Chem. Commun. 1993, 366. (n) Thompson, C. M. Heterocycles 1992, 34, 979. (o) Venit, J. J.; DiPierro, M.; Magnus, P. J. Org. Chem. 1989, 54, 4298.

5. (a) Grigg, R.; Markandu, J.; Surendrakumar, S.; Thornton-Pett, M.; Warnock, W. J. Tetrahedron 1992, 48, 10399. (b) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. (c) Grigg, R.; Dorrity, M. J.; Heaney, F.; Malone, J. F.; Rajviroongit, S.; Sridharan, V.; Surendrakumar, S. Tetrahedron 1991, 47, 8297. (d) Grigg, R.; Heaney, F.; Markandu, J.; Surendrakumar, S.; Thornton-Pett, M.; Warnock, W. J. Tetrahedron 1991, 47, 4007. (e) Armstrong, P.; Grigg, R.; Heaney, F.; Surerndrakumar, S.; Warnock, W. J. Tetrahedron 1991, 47, 4495. (f) Grigg, R.; Heaney, F.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1991, 47, 4477. (g) Grigg, R.; Jordan, M.; Tangthongkum, A.; Einstein, F. W. B.; Jones, T. J. Chem. Soc., Perkin Trans. 1 1984, 47.

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