Stereoselective synthesis of C15-C24 and C25-C30 fragments of dolabelides

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1763-1766

  Desroy, Nicolas ^a   Le Roux, Rémi ^a   Phansavath, Phannarath ^a   Chiummiento, Lucia ^b   Bonini, Carlo ^b   Genêt, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DOLABELIDE A; DOLABELIDE B; DOLABELIDE C; DOLABELIDE D; ESTER DERIVATIVE; HYDROXYL GROUP; MACROLIDE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; HYDROGENATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037463471     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00110-2     Document Type: Article

References (24)

1. Ojika M., Nagoya T., Yamada K. Tetrahedron Lett. 36:1995;7491-7494.
2. Suenaga K., Nagoya T., Shibata T., Kigoshi H., Yamada K. J. Nat. Prod. 60:1997;155-157.
3. Lavergne D., Mordant C., Ratovelomanana-Vidal V., Genêt J.-P. Org. Lett. 3:2001;1909-1912.
4. Poupardin O., Ferreira F., Genêt J.-P., Greck C. Tetrahedron Lett. 42:2001;1523-1526.
5. Phansavath P., Duprat de Paule S., Ratovelomanana-Vidal V., Genêt J.-P. Eur. J. Org. Chem. 2000;3903-3907.
6. Solladié G., Wilb N., Bauder C., Bonini C., Viggiani L., Chiummiento L. J. Org. Chem. 64:1999;5447-5452.
7. Bonini C., Chiummiento L., Funicello M. Tetrahedron: Asymmetry. 12:2001;2755-2760. and references cited therein.
8. Grimaud L., de Mesmay R., Prunet J. Org. Lett. 4:2002;419-421.
9. For a review, see: Genêt, J.-P. In Reductions in Organic Synthesis; Abdel-Magid, A. F., Ed.; ACS Symposium Series 641; American Chemical Society: Washington, DC, 1996; pp. 31-51.
10. For a review, see: Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed. Asymmetric Hydrogenation. Wiley: New York, 2000; pp. 1-110.
11. For the most recent developments and applications on the subject, see the following review: Bonini C., Righi G. Tetrahedron. 58:2002;4981-5021.
12. Duggan A.J., Adams M.A., Brynes P.J., Meinwald J. Tetrahedron Lett. 19:1978;4323-4326.
13. Loubinoux B., Sinnes J.-L., O'Sullivan A.C. J. Chem. Soc., Perkin Trans. 1. 1995;521-525.
14. Madec J., Pfister X., Phansavath P., Ratovelomanana-Vidal V., Genêt J.-P. Tetrahedron. 57:2001;2563-2568.
15. Rathke M.W., Lindert A. J. Am. Chem. Soc. 93:1971;2318-2320.
16. Genêt J.-P., Pinel C., Ratovelomanana-Vidal V., Mallart S., Cano de Andrade M.C., Laffitte J.A. Tetrahedron: Asymmetry. 5:1994;665-674.
17. Ratovelomanana-Vidal V., Genêt J.-P. J. Organomet. Chem. 567:1998;163-171.
18. Fráter G. Helv. Chim. Acta. 62:1979;2825-2828.
19. Seebach D., Wasmuth D. Helv. Chim. Acta. 63:1980;197-200.
20. Wershofen S., Claben A., Scharf H.-D. Liebigs Ann. Chem. 1989;9-18.
21. Gao Y., Hanson R.M., Klunder J.M., Ko S.Y., Masamune H., Sharpless K.B. J. Am. Chem. Soc. 109:1987;5765-5780.
22. Bonini C., Federici C., Rossi L., Righi G. J. Org. Chem. 60:1995;4803-4812.
23. Armstrong R.W., Beau J.-M., Cheon S.H., Christ W.J., Fujioka H., Ham W.-H., Hawkins L.D., Jin H., Kang S.H., Kishi Y., Martinelli M.J., McWhorter W.W. Jr., Mizuno M., Nakata M., Stutz A.E., Talamas F.X., Taniguchi M., Tino J.A., Ueda K., Uenishi J., White J.B., Yonaga M. J. Am. Chem. Soc. 111:1989;7525-7530.
24. For a review, see: Kelly S.E. Trost B.M. Comprehensive Organic Synthesis. 1:1990;729-817 Pergamon Press, Oxford.