Asymmetric synthesis of (2R)- and (2S)-2-iodohexadecanal, natural inhibitors of the thyroid gland metabolism

Tetrahedron

Volumn 52, Issue 31, 1996, Pages 10473-10484

  Jacoby, Claude ^a   Braekman, Jean Claude ^a   Daloze, Désiré ^a  

^a FREE UNIVERSITY OF BRUSSELS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

2 IODOHEXADECANAL; ENZYME INHIBITOR; ORGANOIODINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605921     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00582-0     Document Type: Article

References (38)

1. 1. Pereira, A.; Braekman, J.C.; Dumont, J.E.; and Boeynaems, J.M. J. Biol. Chem. 1990, 265 (28), 17018-17025.
2. 2. a) Panneels, V.; Van den Bergen, H.; Jacoby, C.; Braekman, J.C.; Van Sande, J.; Dumont, J.E.; and Boeynaems, J.M. Mol. Cell Endocrinol. 1994, 102, 167-176.
3. b) Panneels, V.; Van Sande, J.; Van den Bergen, H.; Jacoby, C.; Braekman, J.C.; Dumont, J.E.; and Boeynaems, J.M. Mol. Cell. Endocrinol. 1994, 106, 41-50.
4. 3. a) Martin, V.S.; and Palazon, J.M. Tetrahedron Lett. 1992, 33, 2399-2402.
5. b) Castaldi, G.; Giordano, C.; and Restelli, A. Chemical Abstracts 1988, 108, P 37820s.
6. 4. Alexakis, A.; and Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477-511.
7. 5. a) Naruse, Y.; and Yamamoto, H. Tetrahedron 1988, 44, 6021-6029.
8. b) Sugimura, T.; Yoshikawa, M.; Futagawa, T.; and Tai, A. Tetrahedron 1990, 46, 5955-5966.
9. 6. a) Gassman, P.G.; and Burns, S.J. J. Org. Chem. 1988, 53, 5574-5576.
10. b) Gassman, P.G.; Burns, S.J.; and Pfister, K.B. J. Org. Chem. 1993, 58, 1449-1457.
11. 7. Jacoby, C.; Braekman, J.C.; and Daloze, D. Tetrahedron : Asymmetry 1995, 6, 753-756.
12. 8. For other examples of chiral enol ether formation by acetal opening see ref. 5, 9 and: a) Fioravanti, S.; Loreto, M.A.; Pellacani, L.; and Tardella, P.A. Tetrahedron 1991, 47, 5877-5882.
13. b) Tang, S.; and Kennedy, R.M. Tetrahedron Lett, 1992, 33, 7823-7826.
14. 9. a) Sugimura, T.; Futagawa, T.; Yoshikawa, M.; and Tai, A. Tetrahedron Lett. 1989, 30, 3807-3810.
15. b) Sugimura, T.; Nishiyama, N.; Tai, A.; and Hakushi, T. Tetrahedron : Asymmetry 1993, 4, 43-44.
16. c) Sugimura, T.; Katagiri, T.; and Tai, A. Tetrahedron Lett. 1992, 33, 367-368.
17. 10. a) Stowell, J.C.; and Polito, M.A. J. Org. Chem. 1992, 57, 4560-4562.
18. b) Stowell, J.C.; and Keith, D.R. Synthesis 1979, 132-133.
19. 11. Sammakia, T.; and Berliner, M.A. J. Org. Chem. 1994, 59, 6890-6891.
20. 12. Ellison, R.A.; Lukenbach, E.R.; and Chiu, C.W. Tetrahedron Lett. 1975, 499-502.
21. 13. For recently published deprotection conditions of α-haloaldehyde dimethylacetals see : a) Boni, M.; Ghelfi, F.; Pagnoni, U.M.; and Pinetti, A. Synth. Commun. 1993, 23, 1915-1921.
22. b) Benincasa, M.; Boni, M.; Ghelfi, F.; and Pagnoni, U.M. Synth. Commun. 1995, 25, 1843-1848.
23. 14. This result is in agreement with those already reported, see: Enders, D.; Eichenauer, H.; Baus, U.; Schubert, H.; and Kremer, K.A.M. Tetrahedron 1984, 40, 1345-1359.
24. 15. De Kimpe, N.; and Verhé, R. "The chemistry of α-haloketones, α-haloaldehydes and α-haloimines" edited by Patai, S. and Rappoport, Z., John Wiley & Sons, Chichester, 1988, p. 435.
25. 16. Trost, B.M.; Belletire, J.L.; Godleski, S.; McDougal, P.G.; Balkovec, J.M.; Baldwin, J.J.; Christy, M.E.; Ponticello, G.S.; Varga, S.L.; and Springer, J.P. J. Org. Chem. 1986, 51, 2370-2374.
26. 17. Oppolzer, W.; and Dudfield, P. Tetrahedron Lett. 1985, 26, 5037-5040.
27. 18. a) Groves, J.T.; and Myers, R.S. J. Am. Chem. Soc. 1983, 105, 5791-5796.
28. b) Simon, E.S.; Whitesides, G.M.; Cameron, D.C.; Weitz, D.J.; and Cooney, C.L. J. Org. Chem. 1987, 52, 4042-4044.
29. 19. Ohta, H.; and Tetsukawa, H. J. Chem. Soc., Chem. Commun. 1978, 849-850.
30. 20. a) Castaldi, G.; Cavicchioli, S.; Giordano, C.; and Uggeri, F. J. Org. Chem. 1987, 52, 3018-3027.
31. b) Giordano, C.; Coppi, L.; and Restelli, A. J. Org. Chem. 1990, 55, 5400-5402.
32. c) Giordano, C.; and Coppi, L. J. Org. Chem. 1992, 57, 2765-2766.
33. 21. Dana, G.; Convert, O.; and Perrin, C. J. Org. Chem. 1975, 40, 2133-2135.
34. 22. Horton, D.; Priebe, W.; and Sznaidman, M. Carbohydr. Res. 1990, 205, 71-86.
35. 23. Yamamoto, K.; Shimizu, M.; Yamada, S.; Iwata, S.; and Hoshino, O. J. Org. Chem. 1992, 57, 33-39.
36. 24. Denmark, S.E.; and Almstead, N.G. J. Am. Chem. Soc. 1991, 113, 8089-8110.
37. 25. Ramakrishnan, K.; Oppenhuizen, M.E.; Saunders, S.; and Fisher, J. Biochemistry 1983, 22, 3271-3277.
38. 26. Corey, E.J.; and Suggs, J.W. Tetrahedron Lett. 1975, 2647-2650.