Higher-order cycloaddition reactions in synthesis. Asymmetric assembly of the C5-C11 segment of the ansa bridge of streptovaricin D

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5717-5720

  Rigby, James H ^a   Fales, Kevin R ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STREPTOVARICIN;

ANTIBIOTIC THERAPY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER;

EID: 0032490888     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01183-6     Document Type: Article

References (23)

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2. 2. (a) Wehrli, W.; Staehelin, M. in Antibiotics; Corcoran, J. W.; Hahn, F. E., Eds, Springer-Verlag: New York, 1975; Vol. III, pp. 252-68.
3. (b) Rinehart, K. L., Jr.; Antosz, F. J.; Sasaki, K.; Martin, P. K.; Maheshwari, M. L.; Reusser, F.; Li, L. H.; Moran, D.; Wiley, P. F. Biochemistry 1974, 13, 861.
4. 3. For the first, and to date, only total synthesis of a member of this family, see: Roush, W. R.; Coffey, D. S.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 11331.
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16. 5. Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
17. 6. Munro, J. D.; Pauson, P. L. J. Chem. Soc. 1961, 3475.
18. 13C NMR, IR) and analytical (combustion analysis and/or HRMS) data fully consistent with the assigned structure.
19. 8. For a related observation see: Hudlicky, T.; Luna, H.; Barbieri, G.; Kwart, L. D. J. Am. Chem. Soc. 1988, 110, 4735.
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21. 10. The absolute stereochemistry of this adduct was confirmed by comparison with the corresponding cycloadduct derived from (-)-camphorsultam for which single crystal X-ray analysis had been obtained.
22. 11. Compound 15 could also have arisen from a double oxidation of the bisacetal directly. For somewhat related examples, see: (a) Grieco, P. A.; Oguri, T.; Yokoyama, Y. Tetrahedron Lett. 1978, 419.
23. (b) Sugimura, T.; Fujiwara, Y.; Tai, A. Tetrahedron Lett. 1997, 38, 6019.