An efficient formal synthesis of (-)-balanol by using ruthenium-catalyzed asymmetric hydrogenation

European Journal of Organic Chemistry

Volumn , Issue 23, 2000, Pages 3903-3907

  Phansavath, Phannarath ^a   De Paule, Sébastien Duprat ^a   Ratovelomanana Vidal, Virginie ^a   Genêt, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

( ) Balanol; Asymmetric hydrogenations; Asymmetric synthesis; Dynamic kinetic resolution; Natural products; Ruthenium catalysts

Indexed keywords

BALANOL; HEXAMETHYLENEIMINE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROGENATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033670204     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200012)2000:23<3903::AID-EJOC3903>3.0.CO;2-Q     Document Type: Article

References (37)

1. P. Kulanthaivel, Y. F. Hallock, C. Boros, S. M. Hamilton, W. P. Janzen, L. M. Ballas, C. R. Loomis, J. B. Jiang, B. Katz, J. R. Steiner, J. Clardy, J. Am. Chem. Soc. 1993, 115, 6452-6453.
2. [2a] Y. Nishizuka, Nature 1984, 308, 693-698.
3. [2b] Y. Nishizuka, Science 1986, 233, 305-312.
4. [3a] M. Castagna, Y. Takai, K. Kaibuchi, K. Sano, U. Kikkawa, Y. Nishizuka, J. Biol. Chem. 1982, 257, 7847-7851.
5. [3b] D. Bradshaw, C. Hill, G. S. Nixon, S. E. Wilkinson, Agents Actions 1993, 38, 135-147.
6. [4a] A. Tuch, M. Sanière, Y. Le Merrer, J.-C. Depezay, Tetrahedron: Asymmetry 1996, 7, 2901-2909.
7. [4b] E. Albertini, A. Barco, S. Benetti, C. De Risi, G. P. Pollini, V. Zanirato, Synlett 1996, 29-30.
8. [4c] M. H. Wu, E. N. Jacobsen, Tetrahedron Lett. 1997, 38, 1693-1696.
9. [4d] G. R. Cook, P. S. Shanker, S. L. Peterson, Org. Lett. 1999, 1, 615-617.
10. [4e] C. Herdeis, R. M. Mohareb, R. B. Neder, F. Schwabenländer, J. Tesler, Tetrahedron: Asymmetry 1999, 10, 4521-4537.
11. [4f] A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742.
12. [4g] A. Müller, D. K. Takyar, S. Witt, W. A. König, Liebigs Ann. Chem. 1993, 651-655.
13. [4h] E. Albertini, A. Barco, S. Benetti, C. De Risi, G. Pollini, V. Zanirato, Tetrahedron 1997, 53, 17177-17182.
14. [4i] T. Morie, S. Kato, Heterocycles 1998, 48, 427-431.
15. [4j] C. E. Masse, A. J. Morgan, S. J. Panek, Org. Lett. 2000, 2, 2571-2573.
16. [5a] J. W. Lampe, P. F. Hughes, C. K. Biggers, S. H. Smith, H. Hu, J. Org. Chem. 1994, 59, 5147-5148.
17. [5b] J. W. Lampe, P. F. Hughes, C. K. Biggers, S. H. Smith, H. Hu, J. Org. Chem. 1996, 61, 4572-4581
18. [5c] K. C. Nicolaou, M. E. Bunnage, K. Koide, J. Am. Chem. Soc. 1994, 116, 8402-8403.
19. [5d] K. C. Nicolaou, K. Koide, M. E. Bunnage, Chem. Eur. J. 1995, 1, 454-466.
20. [5e] C. P. Adams, S. M. Fairway, C. J. Hardy, D. E. Hibbs, M. B. Hursthouse, A. D. Morley, B. W. Sharp, N. Vicker, I. Warner, J. Chem. Soc., Perkin Trans. 1 1995, 2355-2362.
21. [5f] D. Tanner, L. Tedenborg, A. Almario, I. Pettersson, I. Csöregh, N. M. Kelly, P. G. Andersson, T. Högberg, Tetrahedron 1997, 53, 4857-4868.
22. [5g] H. Miyabe, M. Torieda, K. Inoue, K. Tajiri, T. Kiguchi, T. Naito, J. Org. Chem. 1998, 63, 4397-4407.
23. [5h] P. Barbier, J. Stadlwieser, Chimia 1996, 50, 530-532.
24. [6a] J.-P. Genêt, S. Jugé, S. Mallart, J. A. Laffitte, 1989, French Patent no. 8911159.
25. [6b] R. Noyori, T. Ikeda, T. Ohkuma, M. Widhalm, M. Kitamura, H. Takaya, S. Akutagawa, N. Sayo, T. Saito, T. Taketomi, H. Kumobayashi, J. Am. Chem. Soc. 1989, 111, 9134-9135.
26. For reviews, see: [6c] R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley, New York, 1994, 74-82 and references cited therein.
27. [6d] J.-P. Genêt, in: Reductions in Organic Synthesis (Ed.: A. F. Abdel Magid), A.C.S. Symposium Series, 1996, 641, 31-51.
28. [6e] V. Ratovelomanana-Vidal, J.-P. Genêt, J. Organomet. Chem. 1998, 567, 163-171.
29. For a mathematical treatment, see: [6f] M. Kitamura, M. Kotunaga, R. Noyori, J. Am. Chem. Soc. 1993, 115, 144.
30. T. Naito, M. Torieda, K. Tajiri, I. Ninomiya, T. Kiguchi, Chem. Pharm. Bull. 1996, 44, 624-626.
31. D. W. Brooks, L. D. L. Lu, S. Masamune, Angew. Chem. Int. Ed. Engl. 1979, 18, 72-74.
32. [9a] J.-P. Genêt, C. Pinel, S. Mallart, S. Jugé, S. Thorimbert, J. A. Laffitte, Tetrahedron: Asymmetry 1991, 2, 555-567.
33. [9b] R. Noyori, M. Tokunaga, M. Kitamura, Bull. Chem. Soc. Jpn. 1995, 68, 36-56.
34. E. Coulon, M. C. Caño de Andrade, V. Ratovelomanana-Vidal, J.-P. Genêt, Tetrahedron Lett. 1998, 39, 6467-6470.
35. [11a] J.-P. Genêt, C. Pinel, V. Ratovelomanana-Vidal, S. Mallart, X. Pfister, M. C. Caño de Andrade, J. A. Laffitte, Tetrahedron: Asymmetry 1994, 5, 665-674.
36. [11b] J.-P. Genêt, C. Pinel, V. Ratovelomanana-Vidal, S. Mallart, X. Pfister, L. Bischoff, M. C. Caño de Andrade, S. Darses, C. Galopin, J. A. Laffitte, Tetrahedron: Asymmetry 1994, 5, 675-690.
37. R: 25.9 min and 30.4 min, (R)-MTPA esters of anti-6 isomers.