Stereoselective synthesis of Macrolactin A analogues. Part 1: The C7-C20 fragment

Tetrahedron

Volumn 52, Issue 36, 1996, Pages 11811-11820

  Benvegnu, Thierry J ^a   Toupet, Loïc J ^b   Grée, René L ^a  

^a CNRS   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; MACROCYCLIC COMPOUND; MACROLACTIN A; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 16044365285     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00666-7     Document Type: Article

References (33)

1. 1-Gustafson, K.; Roman, M.; Fenical, W. J. Am. Chem. Soc., 1989, 111, 7519-7524.
2. 2-Rychnovsky, S.D.; Skalitzky, D.J.; Pathiran, C.; Jensen, P.R.; Fenical, W. J. Am. Chem. Soc., 1992, 114, 671-677.
3. 3-Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett, 1994, 505-506.
4. 4-Donaldson, W.A.; Bell, P.T.; Wang, Z.; Bennett, D.W. Tetrahedron Lett., 1994, 35, 5829-5832.
5. 5-Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Comm., 1996, 26, 559-567. See also a very recent paper: Boyce, R.J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 3501-3504.
6. 5-Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Comm., 1996, 26, 559-567. See also a very recent paper: Boyce, R.J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 3501-3504.
7. 6-Reactions have been carried out from complex 10 in racemic form. Nevertheless only one absolute configuration for complex 10 and its derivatives is represented to allow a better understanding of the diastereoisomeric control.
8. 7-Monpert, A.; Martelli, J.; Grée, R.; Carrié, R. Tetrahedron Lett., 1981, 22, 1961-1963.
9. 8-Grée, R.; Hachem, A.; Grée, D.; Le Floc'h, Y.; Rolland, Y.; Simonet, S.; Verbeuren, T. Sociét́ ADIR et Cie. Eur. Pat. Appl. EP 650,953; Chem. Abst. 1995, 123, 83092 p.
10. 8-Grée, R.; Hachem, A.; Grée, D.; Le Floc'h, Y.; Rolland, Y.; Simonet, S.; Verbeuren, T. Sociét́ ADIR et Cie. Eur. Pat. Appl. EP 650,953; Chem. Abst. 1995, 123, 83092 p.
11. 9-Heathcock, C.H. "The Aldol Reaction" in "Asymmetric Synthesis" J.D. Morrison Ed., Acad. Press New York, 1984, Vol. 3, pp. 111-212.
12. 10-Collman, J.P.; Hegedus, L.S.; Norton, J.R.; Finke, R.G. "Principles and Applications of Organotransition Metal Chemistry", University Science Books, California, 1987; Pearson, A.J. "Metalloorganic Chemistry", John Wiley, New York, 1987; Davies, S.G. "Organotransition Metal Chemistry, Application in Organic Synthesis", Pergamon Press, Oxford, 1982.
13. 10-Collman, J.P.; Hegedus, L.S.; Norton, J.R.; Finke, R.G. "Principles and Applications of Organotransition Metal Chemistry", University Science Books, California, 1987; Pearson, A.J. "Metalloorganic Chemistry", John Wiley, New York, 1987; Davies, S.G. "Organotransition Metal Chemistry, Application in Organic Synthesis", Pergamon Press, Oxford, 1982.
14. 10-Collman, J.P.; Hegedus, L.S.; Norton, J.R.; Finke, R.G. "Principles and Applications of Organotransition Metal Chemistry", University Science Books, California, 1987; Pearson, A.J. "Metalloorganic Chemistry", John Wiley, New York, 1987; Davies, S.G. "Organotransition Metal Chemistry, Application in Organic Synthesis", Pergamon Press, Oxford, 1982.
15. 11-Mukai, C.; Hanaoka, M. Synlett, 1996, 11-17 and references cited therein.
16. 12-(a) Mukai, C.; Cho, W.J.; Hanaoka, M. Tetrahedron Lett., 1989, 30, 7435-7438 ;
17. (b) Mukai, C.; Mihora, A.; Hanaoka, M. Chem. Pharm. Bull., 1991, 39, 2863-2865 ;
18. (c) Mukai, C.; Cho, W.J.; Kim, I.J.; Kido, M.; Hanaoka, M. Tetrahedron, 1991, 47, 3007-3036 ;
19. (d) Mukai, C.; Miyakawa, M.; Mihira, A.; Hanaoka, M. J. Org. Chem., 1992, 57, 2034-2040 ;
20. (e) Mukai, C.; Kim, I.J.; Hanaoka, M. Tetrahedron Asymmetry, 1992, 3, 1007-1010.
21. 13-(a) Roush, W.R.; Park, J.C. J. Org. Chem., 1990, 55, 1143-1156 ;
22. (b) ibid., Tetrahedron Lett., 1990, 37, 4707-4710.
23. 14-(a) Uemura, M.; Minami, T.; Hayashi, Y. Tetrahedron Lett., 1989, 30, 6303-6306 ;
24. (b) Uemura, M.; Minami, T.; Shivo, M.; Hayashi, Y. J. Org. Chem., 1992, 57, 5590-5596.
25. 15-Franck-Neumann, M.; Colson, P.J.; Geoffroy, P.; Taba, K.M. Tetrahedron Lett., 1992, 33, 1903-1906.
26. 16-Teniou, A.; Grée, R. Bull. Soc. Alg. Chim., submitted for publication.
27. 17-(a) Clinton, N.A.; Lillya, C.P. J. Am. Chem. Soc., 1970, 92, 3058-3064 ;
28. (b) Grée, R. Synthesis, 1989, 341-355.
29. 18-(a) Hafner, A.; Von Philipsborn, N.; Salzer, A. Angew. Chem. Int. Ed., 1985, 97, 126-127.
30. (b) Salzer, A.; Schmalle, H.; Stauber, R.; Streiff, S. J. Organomet. Chem. 1991, 408, 403-424.
31. (c) Pinsard, P.; Lellouche, J.P.; Beaucourt, J.P.; Toupet, L.; Schio, L.; Grée, R. J. Organomet. Chem., 1989, 37, 219-231.
32. 19-Evans, D.A.; Chapman, K.T.; Carrera, E.M. J. Am. Chem. Soc., 1988, 110, 3560-3578.
33. 20-Atomic coordinates for these structures have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained from the Director, Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CBZ 1EW, U.K.