Enantioselective synthesis of the macrolide antibiotic oleandomycin aglycon

Journal of the American Chemical Society

Volumn 118, Issue 45, 1996, Pages 11323-11324

  Evans, David A ^a   Kim, Annette S ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; OLEANDOMYCIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0029860478     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963002l     Document Type: Article

References (28)

1. (a) Mulzer, J. Angew. Chem.. Int. Ed. Engl. 1991, 30, 1452-1454.
2. (b) Paterson, I.; Mansuri, M. M. Tetrahedron 1985, 41, 3569-3624.
3. Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukas, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2.
4. (a) Paterson, I.; Norcross, R. D.; Ward, R. A.; Romea, P.; Lister, M. A.J. Am. Chem. Soc. 1994,116, 11287-11314.
5. (b) Paterson, I.; Lister, M. A.; Norcross, R. D. Tetrahedron Lett. 1992, 33, 1767-1770.
6. Paterson, I. Tetrahedron Lett. 1983, 24, 1311-1314.
7. Tatsuta, K.; Ishiyama, T.; Tajima, S.; Koguchi, Y.; Gunji, H. Tetrahedron Lett. 1990, 31, 709-712.
8. (e) Tatsuta, K.; Kobayashi, Y.; Gunji, H. J. Antibiot. 1988, 41, 1520-1523.
9. (f) Tatsuta, K.; Kobayashi, Y.; Gunji, H.; Masuda, H. Tetrahedron Lett. 1988, 29, 3975-3978.
10. (a) Evans, D. A.; Clark, J. S.; Mettemich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 772, 866-868.
11. (b) Evans, D. A.; Ng, H. P.; Clark, J. S.; Rieger, D. L. Tetrahedron 1992, 48, 2127-2142.
12. The sequence of β-ketoimide aldol coupling followed by reduction, thereby establishing four Stereocenters in two steps, has been applied to the recent total syntheses of calyculin, rutamycin, and lonomycin: (a) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434-9453.
13. (b) Evans, D. A.; Ng, H. P.; Rieger, D. L. J. Am. Chem. Soc. 1993, 115, 11446-11459.
14. Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448-3467.
15. (a) The precedent for the stereochemical outcome of this reaction has been established: Sharpless, K. B.; Verhoeven, T. R. Aldrichim. Acta 1979, 12, 63-73.
16. (b) For a general review of directed reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
17. Initial attempts to directly form the C Stereocenter from vinyl metal addition to the aldehyde proved either unselective or resulted in decomposition.
18. The known aldehyde 4 was prepared from Ar-propionyl-4-(R)(phenylmethyl)-oxazolidinone in direct analogy to the reported procedure: Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506-2526.
19. 4 was found to maximize conversion in the coupling of β-ketoimide 2 with aldehyde 4.
20. Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338-344.
21. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Cliem. Soc. 1988, 110, 3560-3578.
22. (l 1) (a) Labadie, J. L.; Stille, J. K. J. Am. Chem. Soc. 1983, 705, 6129-6137 and references cited therein,
23. (b) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 10S, 3033-3040.
24. Reetz, M. T. Acc. Chem. Res. 1993, 26, 462-468 and references cited therein.
25. 3N-HF was prepared from the HF-pyridine complex and EtsN. The excess base was removed in vacua, and the resultant white crystalline solid was stored under argon.
26. (a) Hikota, M.; Sakurai, Y.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1990,31,6367-6370.
27. (b) Hikota, M.; Tone, H.; Horita, K.; Yonemitsu, O. J. Org. Chem. 1990, 55, 7-9.
28. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.