First stereoselective synthesis of the C(1)-C(13) fragment of dolabelides using ruthenium-SYNPHOS®-catalyzed asymmetric hydrogenation reactions

Synlett

Volumn , Issue 3, 2005, Pages 429-432

  Le Roux, Rémi ^a   Desroy, Nicolas ^a   Phansavath, Phannarath ^a   Genêt, Jean Pierre ^a  

^a CNRS   (France)

Author keywords

Asymmetric catalysis; Hydrogenation; Natural products; Ruthenium; Total synthesis

Indexed keywords

CYTOTOXIC AGENT; DOLABELIDE A; DOLABELIDE B; DOLABELIDE C; DOLABELIDE D; ESTER DERIVATIVE; KETONE DERIVATIVE; MACROLIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HORNER WADSWORTH EMMONS REACTION; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 14644410368     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862351     Document Type: Article

References (29)

1. Ojika, M.; Nagoya, T.; Shibata, T.; Yamada, K. Tetrahedron Lett. 1995, 36, 7491.
2. Suenaga, K.; Nagoya, T.; Shibata, T.; Kigoshi, H.; Yamada, K. J. Nat. Prod. 1997, 60, 155.
3. Phansavath, P.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Eur. J. Org. Chem. 2000, 3903.
4. Lavergne, D.; Mordant, C.; Ratovelomanana-Vidal, V.; Genêt, J.-P. Org. Lett. 2001, 3, 1909.
5. Labeeuw, O.; Phansavath, P.; Genêt, J.-P. Tetrahedron: Asymmetry 2004, 15, 1899.
6. (a) Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Tetrahedron Lett. 2003, 44, 823.
7. (b) Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Eur. J. Org. Chem. 2003, 1931.
8. (c) Both antipodes of SYNPHOS® {[2,3,2′,3′-tetrahydro-5, 5′-bi(1,4-benzodioxin)-6,6′-diyl]bis(diphenylphosphane)} are commercially available from Strem Chemicals.
9. Grimaud, L.; de Mesmay, R.; Prunet, J. Org. Lett. 2002. 4, 419.
10. Desroy, N.; Le Roux, R.; Phansavath, P.; Chiummiento, L.; Bonini, C.; Genêt, J.-P. Tetrahedron Lett. 2003, 44, 1763.
11. Schmidt, D. R.; Park, P. K.; Leighton, J. L. Org. Lett. 2003, 5, 3535.
12. Reviews: (a) Genêt, J.-P. In Reductions in Organic Synthesis; Magid, A., Ed.; ACS Symposium Series 641, American Chemical Society: Washington DC, 1996, 31-51.
13. (b) Genêt, J.-P. Acc. Chem. Res. 2003, 36, 908.
14. Noyori, R. Acta Chem. Scand. 1996, 50, 380.
15. Walkup, R. D.; Kane, R. R.; Boatman, P. D. Jr.; Cunningham, R. T. Tetrahedron Lett. 1990, 31, 7587.
16. Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 2318.
17. Genêt, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Caño de Andrade, M. C.; Laffite, J.-A. Tetrahedron: Asymmetry 1994, 5, 665.
18. Genêt, J.-P.; Ratovelomanana-Vidal, V. J. Organomet. Chem. 1998, 567, 163.
19. Frâter, G. Helv. Chim. Acta 1979, 62, 2825.
20. Seebach, D.; Wasmuth, D. Helv. Chim. Acta 1980, 63, 197.
21. Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413.
22. Claffey, M. M.; Hayes, C. J.; Heathcock, C. H. J. Org. Chem. 1999, 64, 8267.
23. Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. J. Chem. Soc., Chem. Commun. 1985, 922.
24. Ohta, T.; Tonomura, Y.; Nozaki, K.; Takaya, H.; Mashima, K. Organometallics 1996, 15, 1521.
25. Mashima, K.; Nakamura, T.; Matsuo, Y.; Tani, K. J. Organomet. Chem. 2000, 607, 51.
26. 12-EtOAc = 8.5:1.5) to give 11 (102 mg, 0.28 mmol, 93%, de = 98%) as a pale yellow oil.
27. For the use of this type of catalyst in total synthesis, see: Fürstner, A.; Dierkes, T.; Thiel, O. R.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286.
28. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
29. Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.