Synthesis and stereochemistry of β-aryl-β-haloacroleins: useful intermediates for the preparation of (Z[hair space]) and (E[hair space])-2-en-4-ynecarbaldehydes and for the synthesis of rubrolides

(Note: The full text of this document is currently only available in the PDF Version )

Damien Prim, Alexia Fuss, Gilbert Kirsch and Artur M. S. Silva


Abstract

The synthesis of α-substituted β-aryl-β-haloacroleins by two different pathways is presented. The determination of their stereochemistry by NOE experiments is reported for the first time. Furthermore, we describe the preparation of 2-en-4-ynecarbaldehydes and access to rubrolide derivatives from β-aryl-β-haloacroleins.


References

  1. R. Sciaky and F. Mancini, Tetrahedron Lett., 1965, 2, 137 CrossRef.
  2. M. G. Lester, V. Petrov and O. Stephenson, Tetrahedron, 1964, 20, 1407 CrossRef CAS.
  3. B. Schulze, G. Kirsten, S. Kirrbach, R. Rahm and H. Heimgarten, Helv. Chim. Acta, 1991, 74, 1059 CAS.
  4. S. Hauptmann and J. Weisflog, J. Prakt. Chem., 1972, 314, 353 CAS.
  5. G. Kirsch, D. Prim, F. Leising and G. Mignani, J. Heterocycl. Chem., 1994, 31, 1005 CAS.
  6. D. Prim, D. Joseph and G. Kirsch, Phosphorus, Sulfur Silicon, 1994, 91, 137 CAS.
  7. P. Cagniant, R. Close, G. Kirsch and D. Cagniant, C. R. Hebd. Acad. Sci., Ser. C, 1975, 281, 187 Search PubMed.
  8. D. Mohlo and M. Giraud, Bull. Soc. Chim. Fr., 1968, 2603.
  9. M. Weissenfels and M. Pulst, Tetrahedron, 1972, 28, 5197 CrossRef CAS.
  10. J. Schmitt, J. J. Panouse, A. Hallot, P. J. Cornu, H. Pluchet and P. Camoy, Bull. Soc. Chim. Fr., 1964, 2753 CAS.
  11. S. M. Jain and R. A. Pawar, Indian J. Chem., Sect. B, 1975, 13, 304 Search PubMed.
  12. G. Alvernhe, B. Langlois, A. Laurent, I. Le Drean, A. Selmi and M. Weissenfels, Tetrahedron Lett., 1991, 32, 643 CrossRef CAS.
  13. A. S. Tasker, J. Med. Chem., 1997, 40, 322 CrossRef CAS.
  14. J. Andrieux, J. P. Battioni, M. Giraud and D. Molho, Bull. Soc. Chim. Fr., 1973, 6, 2093.
  15. H. Hartmann, J. Prakt. Chem., 1971, 313, 1113 CAS.
  16. M. J. Grimwade and M. G. Lester, Tetrahedron, 1969, 25, 4535 CrossRef CAS.
  17. W. Ziegenbein and W. Franke, Angew. Chem., 1959, 71, 573 CAS; W. Ziegenbein and W. Franke, Ger. Pat., 1959, 1. 071. 684; Chem. Abstr., 1961, 55, 16488f Search PubMed.
  18. R. Close, PhD Thesis, University of Metz, 1977; H. Schelhorn, PhD Thesis, University of Leipzig, 1971; J. M. F. Gagan, G. L. Allen and D. Lloyd, J. Chem. Soc. (C), 1970, 2484 Search PubMed; H. Schelhorn, S. Hauptmann and H. Frischleder, Z. Chem., 1973, 13, 97 Search PubMed; M. Weissenfels and M. Pulst, Z. Chem., 1973, 13, 175 RSC.
  19. A. Carpita, A. Lezzi, R. Rossi, F. Marchetti and S. Merlino, Tetrahedron, 1985, 41, 621 CrossRef CAS.
  20. C. M. Marson and P. R. Giles, Synthesis Using Vilsmeier Reagent, CRC Press, NY, 1994 Search PubMed.
  21. Y. V. Quang, P. Cadiot and A. Willemart, C. R. Seances Acad. Sci., 1959, 2356 Search PubMed.
  22. C. Jutz, in Advances in Organic Chemistry, Vol. 9, Iminium Salts in Organic Chemistry, part 1, E. C. Taylor(ed.), J. Wiley, NY, 1976, pp. 65–141 Search PubMed; J. Zemlicka and Z. Arnold, Collect. Czech. Chem. Commun., 1961, 26, 2838 Search PubMed.
  23. J. Bozell and C. E. Vogt, J. Am. Chem. Soc., 1988, 110, 2655 CrossRef CAS.
  24. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 50, 4467 CrossRef.
  25. M. Kotora and E. Negishi, Synthesis, 1997, 121 CrossRef CAS.
  26. E. Dalcanale and F. Montanari, J. Org. Chem., 1986, 51, 567 CrossRef.
  27. K. J. Clark, G. I. Fray, R. H. Jaeger and R. Robinson, Tetrahedron, 1959, 6, 217 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.