Diastereocontrol of nucleophilic attack of the rubanone carbonyl group via remote siloxy tether. Establishing the natural configuration at carbon C-3 of cinchona alkaloid

Tetrahedron

Volumn 53, Issue 27, 1997, Pages 9145-9158

  Langer, Peter ^a   Hoffmann, H M R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; CINCHONA ALKALOID; FUNCTIONAL GROUP;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030913090     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00609-1     Document Type: Article

References (24)

1. Chemical Abstracts name of rubanone 1-H: [1R-[1α,4α,6β(S*)]]-6-[Hydroxy(6-methoxy-4-quinolinyl) methyl]-1-azabicyclo[2.2.2]octane-3-one. Our numbering of Cinchona alkaloids follows the cinchona convention as indicated in Scheme 1.
2. (a) Uskokovic, M. R.; Grethe, G. The Alkaloids, Academic Press, New York, 1973, Vol. 14, 181;
3. (b) Verpoorte, R.; Schripsema, J.; van der Leer, T. The Alkaloids, Academic Press, New York, 1988, Vol. 34, 331;
4. (c) Malcolm, A. D.; David, G. K. Acta Leidensia 1987, 55, 87.
5. (a) von Riesen, C.; Jones, P. G.; Hoffmann, H. M. R. Chem. Eur. J. 1996, 2, 673,
6. (b) von Riesen, C.; Hoffmann, H. M. R. Chem. Eur. J. 1996, 2, 680;
7. (c) Carroll, F. I.; Abraham, P.; Gaetano, K.; Mascarella, S. W.; Wohl, R. A.; Lind, J., Petzoldt, K. J. Chem. Soc. Perkin Trans I 1991, 3017.
8. D' Alonzo, A. J.; Butterfield, J. L.; Drexler, A. P.; Sergio S. L. J. Cardiovascular Pharmacol. 1990, 16, 506.
9. Alcohol 2b has also been prepared by Carroll et al., see reference 3(c).
10. -3], 0.15, -0.13. The full crystallographic data are to be published as NCS in Z. Kristallogr. and may be obtained from the Fachinformationszentrum Karlsruhe, D-76344, Eggenstein-Leopoldshafen (Germany) on quoting the depository number CSD 409000.
11. Langer, P. PhD thesis, University of Hannover 1997; see also Rowan, S. J ; Brady, P. A.; Sanders, J. K. M. Angew. Chem. 1996, 108, 2283.
12. Langer, P. PhD thesis, University of Hannover 1997; see also Rowan, S. J ; Brady, P. A.; Sanders, J. K. M. Angew. Chem. 1996, 108, 2283.
13. (a) Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H. J.; Svendsen, J. S.; Marko, I.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 8069,
14. (b) Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H. J. J. Org. Chem. 1990, 55, 6121.
15. 3J(H-8)-(H-9) 3 Hz suggests an open conformation.
16. endo)-(H-9) (3.8%). The weak NOE (H-3′)-(H-9) (2.3%) indicates that a syn conformation (syn-open or syn-closed) is also populated.
17. endo) for endo-2d, endo-5b, endo-5b and for exo-4b.
18. The relative energies of the TBDS-protected rubanols endo-3b and exo-3b were calculated by MM2 (E(endo-3b) - E(exo-3b) = 0.95 kcal/mol) Thus, rubanol endo-3b is slightly more stable than epimeric exo3b. The energies of the rubanols were sequentially minimized using a MM2 force field (see Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 27) working with the MacroModel© program. A systematic 2000 step Monte Carlo procedure was applied for conformational analysis
19. For stereocontrol of nucleophilic attack to a carbonyl group containing an α-and β-alkoxy substituent, see: Reetz, M. T. Angew. Chem. 1984, 96, 73. Review on complexation of α-and β-alkoxy carbonyls with Lewis acids, see: Reetz, M. T. Acc. Chem. Res. 1993, 26, 462. See also: Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847; Mori, S.; Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1995, 117, 5055; Martin, R.; Pascual, O., Romea, P.; Rovira, R.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1633 See also: Coppola, G. M.; Schuster, H. F. in α-Hydroxy Acids in Enantioselective Syntheses, VCH, Weinheim, 1997.
20. For stereocontrol of nucleophilic attack to a carbonyl group containing an α-and β-alkoxy substituent, see: Reetz, M. T. Angew. Chem. 1984, 96, 73. Review on complexation of α-and β-alkoxy carbonyls with Lewis acids, see: Reetz, M. T. Acc. Chem. Res. 1993, 26, 462. See also: Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847; Mori, S.; Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1995, 117, 5055; Martin, R.; Pascual, O., Romea, P.; Rovira, R.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1633 See also: Coppola, G. M.; Schuster, H. F. in α-Hydroxy Acids in Enantioselective Syntheses, VCH, Weinheim, 1997.
21. For stereocontrol of nucleophilic attack to a carbonyl group containing an α-and β-alkoxy substituent, see: Reetz, M. T. Angew. Chem. 1984, 96, 73. Review on complexation of α-and β-alkoxy carbonyls with Lewis acids, see: Reetz, M. T. Acc. Chem. Res. 1993, 26, 462. See also: Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847; Mori, S.; Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1995, 117, 5055; Martin, R.; Pascual, O., Romea, P.; Rovira, R.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1633 See also: Coppola, G. M.; Schuster, H. F. in α-Hydroxy Acids in Enantioselective Syntheses, VCH, Weinheim, 1997.
22. For stereocontrol of nucleophilic attack to a carbonyl group containing an α-and β-alkoxy substituent, see: Reetz, M. T. Angew. Chem. 1984, 96, 73. Review on complexation of α-and β-alkoxy carbonyls with Lewis acids, see: Reetz, M. T. Acc. Chem. Res. 1993, 26, 462. See also: Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847; Mori, S.; Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1995, 117, 5055; Martin, R.; Pascual, O., Romea, P.; Rovira, R.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1633 See also: Coppola, G. M.; Schuster, H. F. in α-Hydroxy Acids in Enantioselective Syntheses, VCH, Weinheim, 1997.
23. For stereocontrol of nucleophilic attack to a carbonyl group containing an α-and β-alkoxy substituent, see: Reetz, M. T. Angew. Chem. 1984, 96, 73. Review on complexation of α-and β-alkoxy carbonyls with Lewis acids, see: Reetz, M. T. Acc. Chem. Res. 1993, 26, 462. See also: Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847; Mori, S.; Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1995, 117, 5055; Martin, R.; Pascual, O., Romea, P.; Rovira, R.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1633 See also: Coppola, G. M.; Schuster, H. F. in α-Hydroxy Acids in Enantioselective Syntheses, VCH, Weinheim, 1997.
24. For stereocontrol of nucleophilic attack to a carbonyl group containing an α-and β-alkoxy substituent, see: Reetz, M. T. Angew. Chem. 1984, 96, 73. Review on complexation of α-and β-alkoxy carbonyls with Lewis acids, see: Reetz, M. T. Acc. Chem. Res. 1993, 26, 462. See also: Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847; Mori, S.; Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1995, 117, 5055; Martin, R.; Pascual, O., Romea, P.; Rovira, R.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1633 See also: Coppola, G. M.; Schuster, H. F. in α-Hydroxy Acids in Enantioselective Syntheses, VCH, Weinheim, 1997.