Photochemical reactions of chiral 2,3-dihydro-4(1H)-pyridones: asymmetric synthesis of (–)-perhydrohistrionicotoxin

Abstract

The first chiral auxiliary-mediated asymmetric synthesis of (–)-perhydrohistrionicotoxin is described.

References

1. (a) D. L. Comins and S. P. Joseph, Advances in Nitrogen Heterocycles, ed. C. J. Moody, JAI Press, Greenwich, CT, 1996; vol. 2, pp. 251–294; (b) D. L. Comins, S. P. Joseph and X. Chen, Tetrahedron Lett., 1995, 36, 9141; (c) D. L. Comins, S. P. Joseph and D. D. Peters, Tetrahedron Lett., 1995, 36, 9449; (d) D. L. Comins, S. P. Joseph and Y. Zhang, Tetrahedron Lett., 1996, 37, 793; (e) D. L. Comins and L. Guerra-Weltzien, Tetrahedron Lett., 1996, 37, 3807; (f) D. L. Comins, X. Chen and S. P. Joseph, Tetrahedron Lett., 1996, 37, 9275; (g) D. L. Comins, X. Chen and L. A. Morgan, J. Org. Chem., 1997, 62, 7435; (h) D. L. Comins, D. H. LaMunyon and X. Chen, J. Org. Chem., 1997, 62, 8182.
2. D. L. Comins, Y. Lee and P. D. Boyle, Tetrahedron Lett., 1998, 39, 187.
3. P. Guerry and R. Neier, Chimia, 1987, 41, 341; P. Guerry and R. Neier, J. Chem. Soc., Chem. Commun., 1989, 1727; P. Guerry, P. Blanco, H. Brodbeck, O. Pasteris and R. Neier, Helv. Chem. Acta., 1991, 74, 163.
4. D. L. Comins and X. Zheng, J. Chem. Soc., Chem. Commun., 1994, 2681.
5. J. W. Daly and T. F. Spande, Alkaloids: Chemical and Biological Perspectives, ed. S. W. Pelletier, Wiley, New York, 1986; vol. 4, ch. 1, pp. 1–274; J. W. Daly, H. M. Garraffo and T. F. Spande, The Alkaloids, ed. G. A. Cordell, Academic Press: San Diego, CA, 1993; vol. 43, pp. 185–288.
6. For recent synthetic work and leading references on the histrionicotoxins, see: (a) J. D. Winkler and P. M. Hershberger, J. Am. Chem. Soc., 1989, 111, 4852; (b) J. J. Venit, M. DiPierro and P. Magnus, J. Org. Chem., 1989, 54, 4298; (c) G. Stork and K. Zhao, J. Am. Chem. Soc., 1990, 112, 5875; (d) J. Zhu, J. Royer, J.-C. Quirion and H.-P. Husson, Tetrahedron Lett., 1991, 32, 2485; (e) C. M. Thompson, Heterocycles, 1992, 34, 979; (f) P. Compain, J. Gore and J.-M. Vatele, Tetrahedron Lett., 1995, 36, 4063; (g) R. W. Fitch and F. A. Luzzio, Ultrason. Sonochem., 1997, 4, 99.
7. K. Takashashi, B. Witkop, A. Brossi, A. M. Maleque and E. X. Albuquerque, Helv. Chim. Acta, 1982, 65, 252.
8. D. L. Comins, S. P. Joseph and R. R. Goehring, J. Am. Chem. Soc., 1994, 116, 4719.
9. D. L. Comins, L. Guerra-Weltzien and J. M. Salvador, Synlett, 1994, 972; D. L. Comins and L. Guerra-Weltzien, Tetrahedron Lett., 1996, 37, 3807.
10. C. N. Eid and J. P. Konopelski, Tetrahedron Lett., 1991, 32, 461.
11. For reviews on A^1,3 strain, see: R. W. Hoffman, Chem. Rev., 1989, 89, 1841; F. Johnson, Chem. Rev., 1968, 68, 375.
12. D. L. Comins and A. Dehghani, Tetrahedron Lett., 1992, 33, 6299; D. L. Comins, A. Dehghani, C. J. Foti and S. P. Joseph, Org. Synth., 1996, 74, 77.