View PDF Version
 
DOI: 10.1039/A900286C (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1999, 1175-1180

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.