An efficient stereocontrolled synthesis of functionalized chlorodienes and chlorotrienes

Tetrahedron Letters

Volumn 37, Issue 36, 1996, Pages 6547-6550

  Mladenova, Margarita ^a   Alami, Mouâd ^b   Linstrumelle, Gérard ^b  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

Author keywords

chlorodienes; chlorotrienes; palladium; chlorodienal and trienal; chlorodienones and trienones

Indexed keywords

ORGANOCHLORINE DERIVATIVE; POLYENE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0010412276     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01395-0     Document Type: Article

References (27)

1. (a) Uenishi, J.I.; Beau, J.M.; Armstrong, R.W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4756-4758.
2. (b) Duhamel, L.; Pie, G.; Ramondenc, Y. Tetrahedron Lett. 1989, 30, 7377-7380.
3. (c) Chemin, D.; Linstrumelle, G. Tetrahedron 1992, 48, 1943-1952.
4. (d) Alami, M.; Crousse, B.; Linstrumelle, G.; Mambu, L.; Larchevêque, M. SynLett 1993, 217-218.
5. (e) Yokokawa, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1993, 34, 6559-6562.
6. (f) Lipshutz, B.H.; Alami, M.; Susfalk, R.B. Synlett 1993, 693-695.
7. (g) Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
8. (h) Smith, III, A.B.; Maleczka, Jr., R.E.; Leazer, Jr., J.L.; Leahy, J.W.; McCauley, J.A.; Condon, S.M. Tetrahedron Lett. 1994, 35, 4911-4914.
9. Soullez, D.; Pie, G.; Duhamel, L.; Duhamel, P. J. Chem. Soc. Chem. Commun 1995, 563-564.
10. (j) Torrado, A.; Iglesias, B.; Lopez, S.; De Lera, A.R. Tetrahedron 1995, 51, 2435-2454.
11. Denmark, S.E.; Jones, T.K. J. Org. Chem. 1982, 47, 4595-4597.
12. (a) Chemin, D.; Linstrumelle, G. Tetrahedron 1994, 50, 5335-5344.
13. (b) Alami, M.; Gueugnot, S.; Domingues, E.; Linstrumelle, G. Tetrahedron 1995, 51, 1209-1220.
14. Crousse, B.; Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1995, 36, 4245-4248.
15. Cahiez, G.; Alami, M. Manganese dioxide in Encyclopedia of Reagents for Organic Synthesis, Paquette, L.; Ed. Wiley, Chichester 1995, 5, 3229-3235.
16. Arnold, Z.; Zemlica, J. Coll. Czech. Chem. Comm. 1959, 24, 2378-2386.
17. Soullez, D. Ph. D. Thesis, Rouen University, 1994.
18. All new compounds reported herein exhibited spectral data in full accord with assigned structures and gave satisfactory elemental analyses.
19. 13C-NMR (62.9 MHz): δ 197.75, 138.30, 131.90, 130.65, 129.65, 27.55.
20. 13C-NMR (62.9 MHz): δ 198.50, 135.35, 133.25, 128.25, 127.00, 27.30.
21. (a) Overman, L.E.; Knoll, F.M. Tetrahedron Lett. 1979, 321-324.
22. (b) Oehlschlager, A.C.; Mishra, P.; Dhami, S. Can. J. Chem. 1984, 62, 791-797.
23. max = 30400).
24. A non-stereoselective synthesis of unfunctionalized conjugated chlorotrienes has been published, see: (a) Kiehl, A.; Eberhardt, A.; Müllen, K. Liebigs Ann. 1995, 223-230.
25. (b) Charoenying, P.; Davies, P.H.; McKerrecher, D.; Taylor, R.J.K. Tetrahedron Lett. 1996, 37, 1913-1916.
26. max = 36200).
27. max = 38600).