Synthetic studies on bafilomycin A1: Stereoselective synthesis of the C12-C17 fragment and its coupling with the C 1-C11 subunit

Tetrahedron Letters

Volumn 45, Issue 23, 2004, Pages 4533-4537

  Quéron, Emmanuelle ^a   Lett, Robert ^a  

^a SANOFI   (France)

Author keywords

Aldehydes; Diastereoselection; Epoxides; Esterification; Lithium and compounds; Protecting groups; Tin and compounds

Indexed keywords

ALDEHYDE; BAFILOMYCIN A1; CARBON; CARBON 11; CARBOXYLIC ACID; ETHYLENE DERIVATIVE; MACROLIDE; SILANE DERIVATIVE;

ACYLATION; ARTICLE; CHIRALITY; CROSS COUPLING REACTION; CYCLIZATION; ENANTIOSELECTIVITY; ESTERIFICATION; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STILLE REACTION; SYNTHESIS;

EID: 2342628403     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.034     Document Type: Article

References (27)

1. Quéron, E.; Lett, R. Tetrahedron Lett. 2004, 45, preceding paper, doi:10.1016/j.tetlet.2004.04.033
2. Quéron, E.; Lett, R. Tetrahedron Lett. 2004, 45, following paper, doi:10.1016/j.tetlet.2004.04.035
3. Quéron, E. Ph.D. thesis, Paris VI University, 2000
4. Keck G.E., Boden E.P. Tetrahedron Lett. 25:1984;265-268
5. Reetz M.T., Hüllmann M. J. Chem. Soc., Chem. Commun. 1986;1600-1602
6. Chen X., Hortelano E.R., Eliel E.L., Frye S.V. J. Am. Chem. Soc. 114:1992;1778-1784
7. Corey E.J., Wollenberg R.H. J. Am. Chem. Soc. 96:1974;5581-5583
8. Seyferth D., Vick S.C. J. Organomet. Chem. 144:1978;1-12
9. Katsuki T., Sharpless K.B. J. Am. Chem. Soc. 102:1980;5974-5976
10. Johnson R.A., Sharpless K.B. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 6:1991;389-436 Pergamon
11. Katsuki T., Martin V.S. Org. React. 48:1996;1-299
12. Dale J.A., Dull D.L., Mosher H.S. J. Org. Chem. 34:1969;2543-2549
13. Roush W.R., Adam M.A., Peseckis S.M. Tetrahedron Lett. 24:1983;1377-1380
14. Tius M.A., Fauq A.H. J. Org. Chem. 48:1983;4131-4132
15. Chakraborty T.K., Joshi S.P. Tetrahedron Lett. 31:1990;2043-2046
16. Corey E.J., Hopkins P.B. Tetrahedron Lett. 23:1982;4871-4874
17. Omura K., Swern D. Tetrahedron. 34:1978;1651-1660
18. Huang S.L., Omura K., Swern D. Synthesis. 1978;297-299
19. Toshima K., Jyojima T., Yamaguchi H., Noguchi Y., Yoshida T., Murase H., Nakata M., Matsumura S. J. Org. Chem. 62:1997;3271-3284
20. +), 518, 461.
21. Calter, M. A. Ph.D. thesis, Harvard University, 1993
22. Scheidt K.A., Tasaka A., Bannister T.D., Wendt M.D., Roush W.R. Angew. Chem., Int. Ed. 38:1999;1652-1655
23. Scheidt K.A., Bannister T.D., Tasaka A., Wendt M.D., Savall B.M., Fegley G.J., Roush W.R. J. Am. Chem. Soc. 124:2002;6981-6990
24. Hanessian S., Ma J., Wang W., Gai Y. J. Am. Chem. Soc. 123:2001;10200-10206
25. Duncton M.A.J., Pattenden G. J. Chem. Soc., Perkin Trans. 1. 1999;1235-1246
26. Inanaga J., Hirata K., Saeki H., Katsuki T., Yamaguchi M. Bull. Chem. Soc. Jpn. 52:1979;1989-1993
27. +), 1199, 1128