Short syntheses of polyhydroxylated α-alkylated amino acids

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4524-4528

  Grandel, Roland ^a   Kazmaier, Uli ^a   Rominger, Frank ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; OXAMIC ACID; SPHINOFUNGIN; THERMOZYMOCIDIN; UNCLASSIFIED DRUG;

ALKYLATION; ANTIFUNGAL ACTIVITY; ARTICLE; CHIRALITY; DRUG SYNTHESIS; GENE REARRANGEMENT; HYDROXYLATION; NONHUMAN; X RAY CRYSTALLOGRAPHY;

EID: 0032568910     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980205e     Document Type: Article

References (35)

1. (a) Isono, K.; Suzuki, S. Heterocycles 1979, 13, 333.
2. (b) Isono, K.; Asahi, K.; Suzuki, S. J. Am. Chem. Soc. 1969, 91, 7490.
3. Mori, M.; Kakiki, K.; Misato, T. Agric. Biol. Chem. 1974, 38, 699.
4. Becker, J. M.; Covert, N. L.; Shenbagamurthi, P. S.; Steinfeld, A.; Naider, F. Antimicrob. Agents Chemother. 1983, 23, 926.
5. (a) VanMiddlesworth, F.; Giacobbe, R. A.; Lopez, M.; Garrity, G.; Bland, J. A.; Bartizal, K.; Fromtling, R. A.; Polishook, J.; Zweerink, M.; Edison, A. M.; Rozdilsky, W.; Wilson, K. E.; Monaghan, R. L. J. Antibiot. 1992, 45, 861.
6. (b) VanMiddlesworth, F.; Dufresne, C.; Wincott, F. E.; Mosley, R. T.; Wilson, K. E. Tetrahedron Lett. 1992, 33, 297.
7. (a) Bagli, J. F.; Kluepfel, D. J. Org. Chem. 1973, 38, 1253.
8. (b) Fijita, T.; Inoue, K.; Yamamoto, S.; Ikumoto, T.; Sasaki, S.; Toyoma, R.; Chiba, K.; Hoshino, J.; Okumoto, T. J. Antibiot. 1994, 47, 208.
9. Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc., Perkin Trans. 1 1994, 2621.
10. Kazmaier, U. Liebigs Ann./Recl. 1997, 285.
11. (a) Kazmaier, U.; Grandel, R. Synlett 1995, 945.
12. (b) Grandel, R.; Kazmaier, U.; Nuber, B. Liebigs Ann./Recl. 1996, 1143.
13. Grandel, R.; Kazmaier, U. Eur. J. Org. Chem. 1998, 409.
14. Weinreb, S. M.; Demko, D. M.; Lessen, T. A. Tetrahedron Lett. 1986, 27, 2099.
15. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009.
16. (a) Heathcock, C. H. In Modern Synthetic Methods 1992; Scheffold, R., Ed.; VHCA/VCH: Basel, Weinheim, 1992; p 3.
17. (b) Braun, M. In Houben-Weyl: Methods of Organic Synthesis-Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 1603, 1713 and references therein.
18. The product mixtures were analyzed by HPLC and NMR.
19. In contrast, reaction of glycin enolates gave a 1:1 diastereomeric mixture at the α center, probably because of epimerization under the reaction conditions used.
20. (a) Mitsunobu, O. Synthesis 1981, 1.
21. (b) Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, G. D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709.
22. Simon, C. J. Heterocycl. Chem. 1997, 34, 349.
23. Reductive cleavage of the tosyl group: Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741.
24. Recent syntheses of comparable piperidine derivatves: (a) Altenbach, H.-J.; Wischnat, R. Tetrahedron Lett. 1995, 36, 4983. (b) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461.
25. Recent syntheses of comparable piperidine derivatves: (a) Altenbach, H.-J.; Wischnat, R. Tetrahedron Lett. 1995, 36, 4983. (b) Xu, Y.-M.; Zhou, W.-S. Tetrahedron Lett. 1996, 37, 1461.
26. The authors have deposited X-ray structure data at the Cambridge Cystallographic Data Centre. These data can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
27. (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
28. (b) Anh, N. T.; Eisenstein, O. Nouv. J. Chim 1977, 1, 61.
29. Anh, N. T. Top. Curr. Chem. 1980, 88, 145.
30. Kazmaier, U. J. Org. Chem. 1994, 59, 6667.
31. Mori, M.; Chiba, K.; Okita, M.; Kayo, I.; Ban, Y. Tetrahedron 1985, 41, 375.
32. Ito, Y.; Kobayashi, T.; Kawabata, M.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767.
33. Li, W.; Ewing, W. R.; Harris, B. D.; Joullie, M. M. J. Am. Chem. Soc. 1990, 112, 7659.
34. Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265.
35. Mulzer, J. In Organic Synthesis Highlights; Mulzer, J., Altenbach, H.-J., Braun, M., Krohn, K., Reissig, H.-U., Eds.; VCH: Weinheim, 1991; p 243.