Total syntheses of (+)-acutiphycin and (+)-trans-20,21-didehydroacutiphycin

Journal of the American Chemical Society

Volumn 119, Issue 45, 1997, Pages 10935-10946

  Smith III, Amos B ^a   Chen, Sean S Y ^a   Nelson, Frances C ^a   Reichert, Janice M ^a   Salvatore, Brian A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

20,21 DIDEHYDROACUTIPHYCIN; ACUTIPHYCIN; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0030682396     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972497r     Document Type: Article

References (50)

1. Barchi, J. J., Jr.; Moore, R. E.; Patterson, G. M. L. J. Am. Chem. Soc. 1984, 106, 8193.
2. Moore, R. E., University of Hawaii, Mànoa, private communication.
3. Smith, A. B., III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013.
4. Cram, D. J.; Abd Elhafez, F. A. J. Am. Chem. Soc. 1952, 74, 5828. See also: Morrison, J. D.; Mosher, H. S. Asymmetric Organic Reactions; Prentice-Hall: Englewood Cliffs, NJ, 1971.
5. Cram, D. J.; Abd Elhafez, F. A. J. Am. Chem. Soc. 1952, 74, 5828. See also: Morrison, J. D.; Mosher, H. S. Asymmetric Organic Reactions; Prentice-Hall: Englewood Cliffs, NJ, 1971.
6. Fukuyama, T.; Lin, S.-C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050.
7. (a) Still, W. C.; Mitra, A. J. Am. Chem. Soc. 1978, 100, 1927.
8. (b) Nakai, T.; Mikami, K. Chem. Rev. 1986, 56, 885.
9. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
10. Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092.
11. Lane, C. F.; Myatt, H. L.; Daniels, J.; Hopps, H. B. J. Org. Chem. 1974, 39, 3052.
12. Huggins, M. J.; Kubler, D. G. J. Org. Chem. 1975, 40, 2813.
13. (a) Masamune, S.; Ma, P.; Okumoto, H.; Ellingboe, J. W.; Ito, Y. J. Org. Chem. 1984, 49, 2834.
14. (b) Meyers, A. I.; Lawson, J. P. Tetrahedron Lett. 1982, 23, 4883.
15. 13C NMR spectra, as well as appropriate parent ion identification by high-resolution mass spectrometry. (b) In addition, an analytical sample of this compound, obtained by recrystallization or liquid chromatography, gave satisfactory combustion analysis (within 0.4%).
16. Cheng, Y.-S.; Liu, W.-L.; Chen, S.-H. Synthesis 1980, 223.
17. Delongchamps, P. Stereoeleclronic Effects in Organic Chemistry; Baldwin, J. E., Ed.; Pergamon: New York, 1983; pp 4-21.
18. Pfitzner, K. E.; Moffatt, J. G. J. Am. Chem. Soc. 1965, 87, 5670.
19. 12a (mp 80-82 °C).
20. Seyferth, D.; Andrews, S. B. J. Organomet. Chem. 1971, 30, 151.
21. (a) Kallmerten, J.; Balestra, M. Tetrahedron Lett. 1988, 29, 6901.
22. (b) Wittman, M. D.; Kallmerten, J. J. Org. Chem. 1988, 53, 4631.
23. McKillop, A.; Young, D. W. Synthesis 1979, 401.
24. Duggan, A. J.; Adams, M. A.; Brynes, P. J.; Meinwald, J. Tetrahedron Lett. 1978, 45, 4323.
25. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
26. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
27. (a) Dale, J. A; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
28. (b) Ohtani, I.; Kusumi, T.; Ishitsuka, M. O.; Kakisawa, H. Tetrahedron Lett. 1989, 30, 3147.
29. (c) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Org. Chem. 1991, 50, 1296.
30. (d) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
31. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeona, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
32. Hoyer, T.; Kjær, A.; Lykkesfeldt, J. Collect. Czech. Chem. Commun. 1991, 56, 1042.
33. Takano, S.; Akiyama, M.; Sato, S.; Ogasawara, K. Chem. Lett. 1983, 1593.
34. Kocienski, P. J.; Cemigliaro, G.; Feldstein, G. J. Org. Chem. 1977, 42, 353.
35. (a) Hart, D. W.; Blackburn, T. F.; Schwanz, J. J. Am. Chem. Soc. 1975, 97, 679.
36. (b) Carr, D. B.; Schwanz, J. J. Am. Chem. Soc. 1979, 101, 3521.
37. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769.
38. Hong, C. Y.; Kishi, Y. J. Am. Chem. Soc. 1991, 113, 9693.
39. Henrick, C. A. Tetrahedron 1977, 33, 1845.
40. (a) Evans, D. A.; Chapman, K. T. Tetrahedron Lett. 1986, 27, 5939.
41. (b) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
42. (c) Nutaitis, C. F.; Gribble, G. W. Tetrahedron Lett. 1983, 24, 4287.
43. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.
44. (b) Evans, D. A.; Rieger, D. L.; Gase, J. R. Tetrahedron Lett. 1990, 31, 7099.
45. (a) Mukaiyama, T.; Usui, M.; Saigo, K. Chem. Lett. 1976, 49.
46. (b) Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394.
47. (c) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
48. Hayward, C. M.; Yohannes, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 9345.
49. We thank Professor Richard E. Moore, University of Hawaii, Mànoa, for samples of natural (+)-acutiphycin and (+)-tarns-20,21-didehydroacutiphycin.
50. 13C. Optical rotations were obtained with a Perkin-Elmer model 241 polarimeter. High-resolution mass spectra were measured at the University of Pennsylvania Mass Spectrometry Service Center with a VG Micromass 70/70H or VG ZAB-E spectrometer. Microanalyses were performed by Robertson Laboratories, Madison, NJ. High-performance liquid chromatography (HPLC) was performed with a Ranin component analytical/ semipreparative system.