Stereoselective synthesis of 4-amino-3-hydroxy-2-methylpentanoic acids: Stereochemistry of the amino acid occurring in the marine toxin janolusimide

Tetrahedron Asymmetry

Volumn 10, Issue 10, 1999, Pages 1851-1854

  Giordano, Assunta ^a   Spinella, Aldo ^a   Sodano, Guido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 3 HYDROXY 2 METHYLVALERIC ACID; ALANINE DERIVATIVE; BLEOMYCIN DERIVATIVE; JANOLUSIMIDE; MARINE TOXIN; N ALANINAL; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033591131     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00191-3     Document Type: Article

References (21)

1. Boger, D. L.; Ramsey, T. M.; Cai, H.; Hoehn, S. T.; Kozarich, J. W.; Stubbe, J. J. Am. Chem. Soc. 1998, 120, 53-65.
2. Boger, D. L.; Ramsey, T. M.; Cai, H.; Hoehn, S. T.; Stubbe, J. J. Am. Chem. Soc. 1998, 120, 9139-9148.
3. Boger, D. L.; Ramsey T. M.; Cai, H.; Hoehn, S. T.; Stubbe, J. J. Am. Chem. Soc. 1998, 120, 9149-9158.
4. Umezawa, H.; Takita, T.; Saito, S.; Muraoka, Y.; Takahashi, K.; Ekimoto, H.; Minamide, S.; Nishikawa, K.; Fukuoka, T.; Nakatani, T.; Fujii, A.; Matsuda, A. Bleomycin Chemotherapy; Sikic, B.; Rozenweig, M.; Carter, S. K., Eds; Academic Press: Orlando, 1985; p. 289.
5. Sodano, G.; Spinella, A. Tetrahedron Lett. 1986, 27, 2505-2508.
6. Yoshioka, T.; Hara, T.; Takita, T.; Umezawa, H. J. Antibiot. 1974, 27, 356-357.
7. Ohgi, T.; Hecht, S. M. J. Org. Chem. 1981, 46, 1232-1234.
8. Narita, M.; Otsuka, M.; Kobayashi, S.; Ohno, M.; Umezawa, Y.; Morishima, H.; Saito, S.; Takita, T.; Umezawa, H. Tetrahedron Lett. 1982, 23, 525-528.
9. Di Pardo, R. M.; Bock, M. G. Tetrahedron Lett. 1983, 24, 4805-4808.
10. Boger, D. L.; Colletti, S. L.; Honda, T.; Menezes, R. F. J. Am. Chem. Soc. 1994, 116, 5607-5618.
11. Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576.
12. Luly, J. R.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487-1492.
13. Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 5919-5923.
14. Roush, W. R.; Palkowitz, A. D.; Palmer, M. A. J. J. Org. Chem. 1987, 52, 316-318.
15. Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348-6359.
16. Niel, G.; Roux, F.; Maisonnasse, Y.; Maugras, I.; Poncet, J.; Jouin, P. J. Chem. Soc., Perkin Trans. 1 1994, 1275-1280.
17. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
18. Racherla, U. S.; Liao, Y.; Brown, H. C. J. Org. Chem 1992, 57, 6614-6617.
19. Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361-2364.
20. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
21. D=-6.8 (c=1.2).