Enantioselective synthesis of the C11-C24 segment of macrolactin A via organoiron methodology

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9169-9172

  Prahlad, Vadapalli ^a   Donaldson, William A ^a  

^a Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLACTIN A; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; OXIDATION; STEREOCHEMISTRY;

EID: 0030590965     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02150-8     Document Type: Article

References (25)

1. (1) (a) Gustafson, K.; Roman, M.; Fenical, W. J. Am. Chem. Soc..1989, 111, 7519-24;
2. (b) Rychnovsky, S.D.; Skalitzky, D.J.; Pathirana, C.; Jensen, P.R.; Fenical, W. J. Am. Chem. Soc. 1992, 114, 671-7.
3. (2) (a) Rychnovsky, S. D.; Pickering, D. A. Abstracts of papers, 207th National Meeting of the American Chemical Society, San Diego, American Chemical Society: Washington, DC, 1994, ORGN 209;
4. (b) Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett, 1994, 505-6;
5. (c) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett., 1994, 35, 5829-32;
6. (d) Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Syn. Commun., 1996, 26, 559-67;
7. (e) Benvegnu, T.; Toupet, L. J.; Grée, R. Tetrahedron, 1996, 52, 11811-20;
8. (f) Benvegnu, T.; Grée, R. Tetrahedron, 1996, 52, 11821-26.
9. (3) Boyce, R. J.; Pattenden, G. Tetrahedron Lett., 1996, 37, 3501-4.
10. (4) Grée, R.; Tourbah, H.; Carrie, R. Tetrahedron Lett. 1986, 27, 4983-6.
11. (5) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092-3.
12. (6) Roush, W. R.; Park, J. C. Tetrahedron Lett. 1990, 31, 4707-10.
13. (7) Grée, D.; Grée, R.; Lowinger, T. B.; Martelli, J.; Negri, J. T.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 8841-6.
14. (8) Le Gall, T.; Lellouche, J.-P.; Toupet, L.; Beaucourt, J.-P. Tetrahedron Lett. 1989, 30, 6517-20.
15. (9) Brown, H. C.; Unni, M. K. J. Am. Chem. Soc. 1968, 90, 2902-5.
16. 7Fe: C, 46.18; H, 4.17. Found: C, 46.42; H, 4.17.
17. (11) Tomooka, K.; Okinaga, T.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett., 1987, 28, 6335-8.
18. 5Si: C, 48.04; H, 5.25. Found: C, 47.48; H, 5.12.
19. (13) Bell, P. T.; Dasgupta, B.; Donaldson, W. A. J. Organomet. Chem. submitted for publication.
20. 3) δ 172.6, 87.2, 83.0, 67.7, 65.3, 51.6, 45.6, 38.6, 34.1, 28.2, 23.6. This NMR spectral data matches that kindly provided by Dr. René Grée.
21. (15) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-9.
22. (16) Mangeney, P.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1988, 29, 2677-80.
23. + 564.2079).
24. 3 adjunct, reduction of the conjugated diene, and reduction of the ketone functionality.
25. (19) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-78.