Stereoselective synthesis of 11Z-retinal by use of tricarbonyliron complex

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 17, 1996, Pages 2049-2052

  Wada, Akimori ^a   Tanaka, Yukiko ^a   Fujioka, Naoko ^a   Ito, Masayoshi ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

11 CIS RETINAL;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030567869     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00369-1     Document Type: Article

References (16)

1. "The Retinoids", 2nd ed., Sporn, M. B.; Roberts, A. B.; Goodman, D. S.; Eds; Raven Press, Ltd, New York, 1994.
2. Recent review: Rando, R. R. Angew. Chem. Int. Ed. Engl., 1990, 29, 461-480.
3. Heyman, R. A.; Mangelsdorf, D. J.; Dyck, J. A.; Stein, R. B.; Eichele, G.; Evans, R. M.; Thaller, C. Cell, 1992, 68, 397-406, and references cited therein.
4. Although several methods for the formation of 11Z-olefin have been reported, the low yield and the low stereoselectivity are disadvantages that remain to be solved, see; Hosoda, A.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett., 1987, 28, 65-68;
5. Mead, D.; Asato, A. E.; Denny, M.; Liu, R. S. H.; Hanzawa, Y., Taguchi, T.; Yamada, A.; Kobayashi, N.; Hosoda, A.; Kobayashi, Y. Tetrahedron Lett., 1987, 28, 259-262;
6. Trehan, A.; Liu, R. S. H. Tetrahedron Lett., 1988, 29, 419-422.
7. Wada, A.; Hiraishi, S.; Ito, M. Chem. Pharm. Bull., 1994, 42, 757-759.
8. 1H-NMR, IR and MS spectral data were obtained.
9. 2), 5.72 (1H, d, J=11, 8-H), 5.98 (1H, d, J=15, 12-H), 7.09 (1H, dd, J=15,11, 11-H).
10. These compounds were prepared from β-ionone-tricarbonyliron complex analogs (iii) in the same manner described for 3a and the analogs (iii) were obtained from dienylaldehydetricarbonyliron complex (i) by Grignard reaction followed by oxidation using diazocarbonyldipiperidine without decomplexation. For oxidation, see; Saigo, K.; Morikawa, A.; Mukaiyama, T. Bull Chem. Soc. Jpn., 1976, 49, 1656-1658.
11. A similar mechanistic consideration of metalcarbonyl complex has already been reported; Davis, S, G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1, 1990, 393-406;
12. Mukai, C.; Cho, W. J.; Kim, I. J.; Kido, M.; Hanaoka, M. Tetrahedron, 1991, 47, 3007-3036.
13. 2), 1.88 (3H, s, 13-Me), 1.95 (3H, s, 9-Me), 2.02 (1H, d, J=11, 7-H), 4.82 (1H, s, 14-H), 5.28 (1H, d, J=12, 12-H), 5.51 (1H, d, J=11, 8-H), 5.58 (1H, br t, J=12, 11-H).
14. Sato, T.; Matsuoka, H.; Igarashi, T.; Minomura, M.; Murayama, E. J. Org. Chem., 1988, 53, 1207-1212.
15. Liu, R. S. H.; Asato, A. E. Tetrahedron, 1984, 40, 1931-1969;
16. Katsuta, Y.; Sakai, M.; Ito, M. J. Chem. Soc., Perkin Trans. 1, 1993, 2185-2192.