Palladium-catalyzed coupling reaction of an enol nonaflate with (vinyl)tributylstannanes and acetylenes: A highly stereoselective synthesis of 8,18-13C2-labeled retinal

Synthesis

Volumn , Issue 10, 2005, Pages 1581-1588

  Wada, Akimori ^a   Ieki, Yasuhiro ^a   Nakamura, Saeko ^a   Ito, Masayoshi ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Alkenyl stannane; Coupling reaction; Labeled retinal; Solid state NMR; Vinyl nonaflate

Indexed keywords

ACETYLENE; CARBON; CATALYSIS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CROSS-COUPLING REACTIONS; E-OLEFIN; ENOL NONAFLATE; VINYL NONAFLATE;

PALLADIUM;

(VINYL)TRIBUTYLSTANNANE DERIVATIVE; ACETYLENE; ALKENE; ALKENYL GROUP; CARBON; CARBON 13; ENOL NONAFLATE; ORGANOTIN COMPOUND; PALLADIUM; RETINAL; STANNANE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLID STATE; STEREOCHEMISTRY; SYNTHESIS;

EID: 22244463214     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865294     Document Type: Article

References (42)

1. Retinoids and related compounds: Part 28. See also Part 27: Wada, A.; Fukunaga, K.; Ito, M.; Mizuguchi, Y.; Nakagawa, K.; Okano, T. Bioorg. Med. Chem. 2004, 12, 3931.
2. The chromophore of rhodopsin is (11Z)-retinal, and those of the others are (all-E)-retinal, respectively: (a) Yoshizawa, T.; Wald, G. Nature (London) 1963, 197, 1279.
3. (b) Hara, T.; Hara, R. Nature (London) 1968, 219, 450.
4. (c) Stoeckenius, W.; Bogomolni, R. A. Annu. Rev. Biochem. 1982, 51, 587.
5. Bogomolni, R. A.; Spudich, J. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 6250.
6. (e) Tomioka, H.; Takahashi, T.; Kamo, N.; Kobatake, Y. Biochem. Biophys. Res. Commun. 1986, 139, 389.
7. (a) Arnaboldi, M.; Motto, M. G.; Tsujimoto, K.; Balogh-Nair, V.; Nakanishi, K. J. Am. Chem. Soc. 1979, 101, 7082.
8. (b) Akita, H.; Tanis, S. P.; Adams, M.; Balogh-Nair, V.; Nakanishi, K. J. Am. Chem. Soc. 1980, 102, 6370.
9. (c) van der Steen, R.; Biesheuvel, P. L.; Mathies, R. A.; Lugtenburg, J. J. Am. Chem. Soc. 1986, 108, 6410.
10. (d) van der Steen, R.; Groesbeek, M.; van Amsterdam, L. J. P.; Lugtenburg, J.; van Oostrum, J.; de Grip, W. J. J. Am. Chem. Soc. 1989, 108, 20.
11. (e) van der Steen, R.; Biesheuvel, P. L.; Erkelens, C.; Mathies, R. A.; Lugtenburg, J. J. Am. Chem. Soc. 1989, 108, 83.
12. (f) Hanzawa, Y.; Suzuki, M.; Kobayashi, Y.; Taguchi, T. Chem. Pharm. Bull. 1991, 39, 1035.
13. (g) Spijker-Assink, M. B.; Robijn, G. W.; Ippel, J. H.; Lugtenburg, J.; Groen, B. H.; van Dam, K. Recl. Trav. Chim. Pays-Bas 1992, 111, 29.
14. (h) Groesbeek, M.; Robijn, G. W.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1992, 111, 92.
15. (i) Caldwell, C. G.; Derguiri, F.; Bigge, C. F.; Chen, A.-H.; Hu, S.; Wang, J.; Sastry, L.; Nakanishi, K. J. Org. Chem. 1993, 62, 3638.
16. (j) Wada, A.; Tsutsumi, M.; Inatomi, Y.; Imai, H.; Shichida, Y.; Ito, M. Chem. Pharm. Bull. 1995, 43, 1419.
17. (k) Wada, A.; Sakai, M.; Kinumi, T.; Tsujimoto, K.; Ito, M. J. Org. Chem. 1995, 59, 6922.
18. McDermott, A. E.; Creuzet, F.; Gebhard, R.; van der Hoef, K.; Levitt, M. H.; Herzfeld, J.; Lugtenburg, J.; Griffin, R. G. Biochemistry 1994, 33, 6129.
19. Thompson, L. K.; McDermott, A. E.; Rapp, J.; van der Wielen, C. M.; Lugtenburg, J.; Herzfeld, J.; Griffin, R. G. Biochemistry 1992, 31, 7931.
20. Wada, A.; Akai, A.; Goshima, T.; Takahashi, T.; Ito, M. Bioorg. Med. Chem. Lett. 1998, 8, 1365.
21. For a review, see: Ritter, K. Synthesis 1993, 735.
22. (a) Yasuda, N.; Xavier, L.; Rieger, D. L.; Li, Y.; DeCamp, A. E.; Dolling, U.-H. Tetrahedron Lett. 1993, 34, 3211.
23. (b) Nicolaou, K. C.; Sato, M.; Miller, N. D.; Gunzner, J. L.; Renaud, J.; Untersteller, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 889.
24. (c) Sasaki, M.; Fuwa, H.; Inoue, M.; Tachibana, K. Tetrahedron Lett. 1998, 39, 9027.
25. Wada, A.; Nomoto, Y.; Tano, K.; Yamashita, E.; Ito, M. Chem. Pharm. Bull. 2000, 48, 1391.
26. For the Heck coupling of enol nonaflate, see: (a) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545.
27. (b) Webel, M.; Reissig, H.-U. Synlett 1997, 1141.
28. (c) Bräse, S. Synlett 1999, 1654.
29. (d) Lyapkalo, I. M.; Webel, M.; Reissig, H.-U. Synlett 2001, 1293.
30. (e) Lyapkalo, I. M.; Webel, M.; Reissig, H.-U. Eur. J. Org. Chem. 2001, 4189.
31. For Stille, Suzuki and Sonogashira couplings of aryl nonaflates, see: (a) Rottläbder, M.; Knochel, P. J. Org. Chem. 1998, 63, 203.
32. (b) Stoltz, B. M.; Kano, T.; Corey, E. J. J. Am. Chem. Soc. 2000, 122, 9044.
33. (c) Bellina, F.; Ciucci, D.; Vergamini, P.; Rossi, R. Tetrahedron 2000, 56, 2533.
34. Wada, A.; Ieki, Y.; Ito, M. Synlett 2002, 1061.
35. Engler, T. A.; Sampath, U.; Naganathan, S.; Velde, D. V.; Takuasgawa, F. J. Org. Chem. 1989, 54, 5712.
36. Subramanian, L. R.; Bentz, H.; Hanack, M. Synthesis 1973, 293.
37. In the cases of the trisubstituted olefins 5d and 5e, their stereochemistry was determined after conversion to the corresponding aldehyde by oxidation, see: Wada, A.; Hiraishi, S.; Takamura, N.; Date, T.; Aoe, K.; Ito, M. J. Org. Chem. 1997, 62, 4343.
38. Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773.
39. (a) Hirsch, E.; Hünig, S.; Reißig, H.-U. Chem. Ber. 1982, 115, 3687.
40. (b) Subramanian, L. R.; Bentz, H.; Hanack, M. Synthesis 1973, 293.
41. Bennai, Y. L. J. Org. Chem. 1996, 61, 3542.
42. Labeled positions were based on the retinoid numbering system.