Total syntheses of (±)-cherylline and (±)-latifine

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Axel Couture, Eric Deniau, Stéphane Lebrun and Pierre Grandclaudon


Abstract

A new total synthesis of the two phenolic alkaloids (±)-cherylline 1 and (±)-latifine 2 isolated from Crinum species is described. The two key steps in the elaboration of these natural products are an anionic variant of the Fries rearrangement which gives access to the congested o-aroylbenzoic acid derivatives 26 and 27, and an intramolecular Horner reaction involving the corresponding N-phosphorylmethylbenzamide derivatives 8 and 9.


References

  1. A. Brossi, G. Grethe, S. Tertel, S. C. Wildman and D. T. Bailey, J. Org. Chem., 1970, 36, 1100 CrossRef CAS.
  2. S. Kobayashi, T. Tokumoto and Z. Taira, J Chem. Soc., Chem. Commun., 1984, 1043 RSC.
  3. C. Fuganti, in The Alkaloids, ed. R. H. F. Manske, Academic Press, New York, 1975, vol. XV, p. 139 Search PubMed.
  4. M. Shamma and J. L. Moniot, Isoquinoline Alkaloids Research 1972–1977, Plenum Press, New York, 1978, p. 389 Search PubMed.
  5. F. A. Kincl, V. Troncoso and G. Rosenkranz, J. Org. Chem., 1957, 22, 574 CrossRef CAS.
  6. T. Kametani, The Chemistry of the Isoquinoline Alkaloids, The Sendai Institute of Heterocyclic Chemistry, Sendai, 1974, vol. 2, p. 321 Search PubMed.
  7. H. Hara, R. Shirai, O. Hoshino and B. Umezawa, Heterocycles, 1983, 20, 1945 CAS and references cited therein.
  8. Annual Reports in Medicinal Chemistry, ed. H.-J. Hess, Academic Press, New York, 1978, vol. 13, p. 6; 1978, vol. 14, p. 1; 1981, vol. 16, p. 89 and references cited therein Search PubMed.
  9. J. D. Kohli and L. I. Goldberg, J. Pharm. Pharmacol., 1980, 32, 225 Search PubMed.
  10. J. A. Poat, G. N. Woodruff and K. J. Watling, J. Pharm. Pharmacol., 1978, 30, 495 Search PubMed.
  11. B. Costall and R. J. Naylor, J. Pharm. Pharmacol., 1978, 30, 514 Search PubMed.
  12. J. N. Jacob, D. E. Nichols, J. D. Kohli and D. Glock, J. Med. Chem., 1981, 24, 1013 CrossRef CAS.
  13. (a) M. A. Schwartz and S. W. Scott, J. Org. Chem., 1971, 36, 1827 CrossRef CAS; (b) T. Kametani, K. Takahashi and C. V. Lock, Tetrahedron, 1975, 31, 235 CrossRef CAS; (c) D. J. Hart, P. A. Cain and D. A. Evans, J. Am. Chem. Soc., 1978, 100, 1548 CrossRef CAS; (d) H. Irie, A. Shiina, T. Fushimi, J. Katakawa, N. Fujii and H. Yajima, Chem. Lett., 1980, 875 CAS; (e) T. Kametani, K. Higashiyama, T. Honda and H. Otomasu, J. Chem. Soc., Perkin Trans. 1, 1982, 2935 RSC; (f) J. Katakawa, H. Yoshimatsu, M. Yoshida, Y. Zhang, H. Irie and H. Yasima, Chem. Pharm. Bull., 1988, 36, 3928 CAS.
  14. S. Kobayashi, T. Tokumoto, S. Iguchi, M. Kihara, Y. Imakura and Z. Taira, J. Chem. Res. (S), 1986, 280 (J. Chem. Res. (M), 1986, 2444) Search PubMed.
  15. A. Brossi and S. Tertel, Tetrahedron Lett., 1970, 417 CrossRef CAS.
  16. T. Nomoto, N. Nasui and H. Takayama, J. Chem. Soc., Chem. Commun., 1984, 1646 RSC.
  17. S. Takano, M. Akiyama and K. Ogasawara, J. Chem. Soc., Perkin Trans. 1, 1985, 2447 RSC.
  18. (a) A. Couture, E. Deniau and P. Grandclaudon, Tetrahedron Lett., 1993, 34, 1479 CrossRef CAS; (b) B. H. Bakker, D. S. Tjin A-Lim and A. van der Gen, Tetrahedron Lett., 1984, 25, 4259 CrossRef CAS; (c) A. Couture, E. Deniau and P. Grandclaudon, Tetrahedron, 1997, 53, 10303 CrossRef CAS; (d) A. Couture, E. Deniau, C. Hoarau and P. Grandclaudon, J. Org. Chem., 1998, 63, 3128 CrossRef CAS.
  19. (a) A. Couture, E. Deniau, Y. Gimbert and P. Grandclaudon, J. Chem. Soc., Perkin Trans. 1, 1993, 2463 RSC; (b) A. Couture, E. Deniau, P. Grandclaudon and P. Woisel, Tetrahedron, 1996, 52, 4433 CrossRef CAS.
  20. S. Horne and R. Rodrigo, J. Chem. Soc., Chem. Commun., 1992, 164 RSC.
  21. W. E. Parham and Y. A. Sayed, J. Org. Chem., 1974, 39, 2053 CrossRef CAS.
  22. W. P. Griffith and S. V. Ley, Aldrichim. Acta, 1990, 23, 13 Search PubMed.
  23. B. S. Bal, W. E. Childers and H. W. Pinnick, Tetrahedron, 1981, 37, 2091 CrossRef.
  24. A. Couture, E. Deniau, P. Grandclaudon and S. Lebrun, Tetrahedron Lett., 1996, 37, 7749 CrossRef.
  25. R. E. Bolton, C. J. Moody, C. W. Rees and G. Tojo, J. Chem. Soc., Perkin Trans. 1, 1987, 931 RSC.
  26. M. L. Scarpati, A. Bianco and R. L. Scalzo, Synth. Commun., 1991, 849 CAS.
  27. M. R. Paléo, C. Lamas, L. Castedo and D. Dominguez, J. Org. Chem., 1992, 57, 2029 CrossRef CAS.
  28. T. Kametani, K. Fukumoto, S. Shibuya, H. Nemoto, T. Nakano, T. Sugahara, T. Takahashi, Y. Aizawa and M. Toriyama, J. Chem. Soc., Perkin Trans. 1, 1972, 1435 RSC.
  29. A. K. Mohammad-Ali, T. H. Chan, A. W. Thomas, B. Jewett and G. M. Strunz, Can. J. Chem., 1994, 72, 2137 CAS.
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