Desymmetrization of 3-dimethyl(phenyl)silyl glutaric anhydride with Evans' oxazolidinone: An application to stereocontrolled synthesis of the antifungal agent (+)-preussin

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 3, 1999, Pages 265-270

  Verma, Rekha ^a   Ghosh, Sunil K ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001275805     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808840c     Document Type: Article

References (28)

1. (a) R. E. Schwartz, J. Liesch, O. Hensens, L. Zitano, S. Honeycutt, G. Garrity, and R. A. Fromtling, J. Antihiot., 1988, 41, 1774;
2. (b) R. E. Schwartz, J. C. Onishi, R. L. Monaghan, J. M. Liesch, and O. D. Hensens, US Patent 4 847 284, 1989;
3. J. H. Johnson, D. W. Phillipson, and A. D. Kahle, J. Antibiot., 1989,42, 1184.
4. C. S. Pak, and G. H. Lee, J. Org. Chem., 1991,56, 1128.
5. P. de-Armas, F. Garcia-Tellado, J. J. Marrero-Tellado, and J. Robles, Tetrahedron Lett., 1998, 39, 131.
6. H. Yoda, M. Yamazaki, and K. Takabe, Tetrahedron: Asymmetry, 1996,7,373.
7. (a)P. L. McGraneandT. Livinghouse, J Am. Client. Suc., 1993,115, 11485;
8. (b) M. Overhand, and S. M. Hecht, J. Org. Chem., 1994, 59, 4721;
9. W. Dengand L. E. Overman, J. Am. Cliem. Soc., 1994,116, 11241;
10. C. Beier, and E. Schaumann, Synthesis, 1997, 1296.
11. M. Shimazaki, F. Okazaki, F. Nakajima, T. Ishikawa, and A. Ohta, Heterocycles, 1993,36, 1823.
12. A. Kanazawa, S. Gillet, P. Delair, and A. E. Greene, J. Org. Chem., 1998,63.4660.
13. R. Verma, S. Mithran, and S. K. Ghosh, please see the preceding article 8/08838A.
14. (a) T. Rosen, and C. H. Heathcock, J. Am. Chem. Sue., 1985, 107, 3731;
15. (b) D. S. Karanewsky, M. F. Malley, and J. Z. Gougoutas, J. Org. Chem., 1991, 56, 3744.
16. For stereoselective a-alkylation of -hydroxy acids; see: G. Fr'ater, Heir. Chim. Acta, 1979, 62, 2825;
17. D. Seebach, and D. Wasmuth, Heir. Chim. Acta, 1980, 63, 197.
18. For a review, see: I. Fleming, A. Barbero, and D. Walter, Client. Rer., 1997, 97, 2063.
19. See also: I. Fleming, R. Henning, D. C. Parker, H. E. Plaut, and P. E. J. Sanderson, J. Chem. Soc., Perkin Trans. I, 1995,317.
20. R. A. N. C. Crump, I. Fleming, J. H. M. Hill, D. Parker, N. L. Reddy, and D. Waterson, J. Chem. Soc., Perkin Trans, l, 1992, 3277.
21. R. Verma, and S. K.. Ghosh, J. Cliein. Soc., Perkin Trans, l, 1998, 2377.
22. R. Verma, and S. K. Ghosh, Cliein. Commun., 1997, 1601.
23. (a) D. A. Evans, and A. S. Kim, in Encyclopedia of reagents for organic synthesis, ed. L. A. Paquctte, Wiley, NY, 1995, vol. 11, p. 345;
24. (b) D. Ager, I. Prakash, and D. R. Schaad, Client. Rer., 1996, 96.835;
25. D. A. Evans, T. C. Briton, 1 A. Ellman, and R. L. Dorow, J. Am. Chem. Soc., 1990, 112, 4011.
26. E. Kaiser, ST., F. Pickart, T. Kubiak, J. R Tarn, and R. B. Merrifield, J. Org. C/u
27. T. H. Chan, M. A. Brook, and T. Chaly, Synthesis. 1983,203.
28. H. E. Baumgarten, H. L. Smith, and A. Staklis, J. Orç. Client., 1975, 40, 3555.