An iterative procedure for the synthesis of conjugated ω-chlorotrienoic and -tetraenoic esters and related derivatives

European Journal of Organic Chemistry

Volumn , Issue 14, 2003, Pages 2713-2718

  Mladenova, Margarita ^a   Tavlinova, Maya ^a   Momchev, Momcho ^a   Alami, Mouâd ^b   Ourévitch, Michèle ^b   Brion, Jean Daniel ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^b UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

Asymmetric synthesis; Chlorine; Enynes; Wittig reactions

Indexed keywords

ALLYL ALCOHOL; CHLORINE DERIVATIVE; CHLORODIENOL; CHLOROENYNOL; OMEGA CHLOROTETRAENOIC ESTER; OMEGA CHLOROTRIENOIC ESTER; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

EID: 0041344672     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300110     Document Type: Article

References (39)

1. J. Uenishi, R. Kawahama, O. Yonemitsu, J. Tsuji, J. Org. Chem. 1996, 61, 5716-5717.
2. [2a] A. Kiehl, A. Eberhardt, K. Müllen, Liebigs Ann. 1995, 223-230.
3. [2b] Y. Pazos, A. R. de Lera, Tetrahedron Lett. 1999, 40, 8287-8290.
4. [2c] A. K. Mapp, C. H. Heathcock, J. Org. Chem. 1999, 64, 23-27.
5. [3a] D. R. Williams, K. Nishitani, W. Bennett, S. Y. Sit, Tetrahedron Lett. 1981, 22, 3745-3748.
6. [3b] L. Duhamel, G. Plé, Y. Ramondenc, Tetrahedron Lett. 1989, 30, 7377-7380.
7. [3c] D. Soullez, G. Plé, L. Duhamel, P. Duhamel, J. Chem. Soc., Chem. Commun. 1995, 563-564.
8. [3d] P. Charoenying, D. H. Davies, D. McKerrecher, R. J. K. Taylor, Tetrahedron Lett. 1996, 37, 1913-1916.
9. [3e] G. Macdonald, N. J. Lewis, R. J. K. Taylor, Chem. Commun. 1996, 2647-2648.
10. [3f] D. Soullez, G. Plé, L. Duhamel, J. Chem. Soc., Perkin Trans. 1 1997, 1639-1645.
11. [3g] G. Macdonald, L. Alcaraz, X. Wei, N. J. Lewis, R. J. K. Taylor, Tetrahedron 1998, 54, 9823-9836.
12. [3h] B. H. Lipshutz, B. Ullman, C. Lindsley, S. Pecchi, D. J. Buzard, D. Dickson, J. Org. Chem. 1998, 63, 6092-6093.
13. [3i] P. Villiers, N. Vicart, Y. Ramondenc, G. Plé, Tetrahedron Lett. 1999, 40, 8781-8784.
14. [3j] P. Villiers, D. Soullez, Y. Ramondenc, G. Plé, Tetrahedron 1999, 55, 14031-14042.
15. [3k] P. Villiers, N. Vicart, Y. Ramondenc, G. Pié, Eur. J. Org. Chem. 2001, 561-574.
16. [3l] E. Quesada, A. U. Acuna, F. Amat-Guerri, Angew. Chem. Int. Ed. 2001, 40, 2095-2097.
17. [4a] M. Alami, G. Linstrumelle, Tetrahedron Lett. 1991, 32, 6109-6112.
18. [4b] P. Ramiandrasoa, B. Bréhon, A. Thivet, M. Alami, G. Cahiez, Tetrahedron Lett. 1997, 38, 2447-2450.
19. [4c] M. Alami, P. Ramiandrasoa, G. Cahiez, Synlett 1998, 325-327.
20. [4d] M. Alami, B. Crousse, F. Ferri, J. Organomet. Chem. 2001, 624, 114-123.
21. For a review, see: [5a] M. Alami, J. F. Peyrat, J. D. Brion, Synthesis 2000, 1499-1518.
22. [5b] B. Crousse, M. Mladenova, P. Ducept, M. Alami, G. Linstrumelle, Tetrahedron 1999, 55, 4353-4368.
23. [5c] B. Crousse, M. Alami, G. Linstrumelle, Tetrahedron Lett. 1995, 36, 4245-4248.
24. B. Crousse, M. Alami, G. Linstrumelle, Tetrahedron Lett. 1997, 38, 5297-5300.
25. M. Mladenova, M. Alami, G. Linstrumelle, Tetrahedron Lett. 1996, 37, 6547-6550.
26. E. J. Corey, N. W. Gilman, B. E. Ganem, J. Am. Chem. Soc. 1968, 90, 5616-5617.
27. X. Wei, R. J. K. Taylor, J. Org. Chem. 2000, 65, 616-620.
28. [10a] L. Crombie, M. A. Horsham, R. M. Jarrett, Tetrahedron Lett. 1989, 30, 4299-4302.
29. [10b] I. Uemura, H. Miyagawa, T. Ueno, Tetrahedron 2002, 58, 2351-2358.
30. [11a] S. D. Rychnovsky, Chem. Rev. 1995, 95, 2021-2040.
31. [11b] M. Gill, Nat. Prod. Rep. 1994, 67-90.
32. [11c] P. Wipf, P. D. G. Coish, Tetrahedron Lett. 1997, 38, 5073-5076.
33. [11d] R. Mukhopadhyay, N. G. Kundu, Tetrahedron 2001, 57, 9475-9480.
34. M. B. Sporn, A. B. Roberts, D. S. Goodman, The Retinoids, Biology, Chemistry and Medecine 2nd ed., Raven Press, New York, 1994.
35. M. Alami, J. F. Peyrat, J. D. Brion, Tetrahedron Lett. 2002, 43, 3007-3010.
36. M. Mladenova, M. Alami, G. Linstrumelle, Synth. Commun. 1996, 26, 2831-2842.
37. D. Chemin, G. Linstrumelle, Tetrahedron 1994, 50, 5335-5344.
38. 2 used; very good results were obtained with manganese dioxide prepared according to: [16a] H. B. Henbest, E. R. H. Jones, T. C. Owen, J. Chem. Soc. 1957, 4909-4912. For a review see: [16b] G. Cahiez, M. Alami, "Manganese dioxide", in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. Paquette), Wiley, Chichester, 1995, vol. 5, p. 3229-3235.
39. 2 used; very good results were obtained with manganese dioxide prepared according to: [16a] H. B. Henbest, E. R. H. Jones, T. C. Owen, J. Chem. Soc. 1957, 4909-4912. For a review see: [16b] G. Cahiez, M. Alami, "Manganese dioxide", in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. Paquette), Wiley, Chichester, 1995, vol. 5, p. 3229-3235.