Asymmetric synthesis of (2S,6S)- and meso-(2S,6R)-diaminopimelic acids from enantiopure bis(sulfinimines)

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 3248-3251

  Davis, Franklin A ^a   Srirajan, Vaidyanathan ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINOPIMELIC ACID;

AMINO ACID SYNTHESIS; DECARBOXYLATION; DRUG CYTOTOXICITY; HYDROGENATION; NOTE; POLYMERIZATION; STEREOCHEMISTRY;

CHROMATOGRAPHY, THIN LAYER; DIAMINOPIMELIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; SULFOXIDES;

EID: 0034686062     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000038u     Document Type: Note

References (39)

1. For a review on DAP metabolism see: (a) Cox, R. J. Nat. Prod. Rep. 1996, 13, 29. (b) Scapin, G.; Blanchard, J. S. Adv. Enzymol. Relt. Areas Mol. Biol. 1998, 72, 279.
2. For a review on DAP metabolism see: (a) Cox, R. J. Nat. Prod. Rep. 1996, 13, 29. (b) Scapin, G.; Blanchard, J. S. Adv. Enzymol. Relt. Areas Mol. Biol. 1998, 72, 279.
3. (a) Sutherland, A.; Vederas, J. Chem. Soc. Chem. Commun. 1999, 1739.
4. (b) Sutherland, A.; Caplan, J. F.; Vederas, J. C. J. Chem. Soc. Chem. Commun. 1999, 555.
5. (c) Gao, Y.; Lane- Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133.
6. (d) Cox, R. J.; Sherwin, W. A.; Lam, L. K. P.; Vederas, J. C. J. Am. Chem. Soc. 1996, 118, 7449.
7. (e) Song, Y.; Niederer, D.; Lane-Bell, P. M,; Lam, L. K. P.; Crawley, S.; Palcic, M. M.; Pickard, M. A.; Pruess, D. L.; Vederas, J. C. J. Org. Chem. 1994, 592, 5784.
8. (f) Abbott, S. D.; Lane-Bell, P.; Sidhu, K. P. S.; Vederas, J. C. J. Am. Chem. Soc. 1994, 116, 6513.
9. (g) Gelb, M. H.; Lin, Y.; Pickard, M. A.; Song, Y.; Vederas, J. C. J. Am. Chem. Soc. 1990, 112, 4932.
10. (a) Williams, R. M.; Liu, J. J. Org. Chem. 1998, 63, 2130.
11. (b) Williams, R. M.; Fegley, G. L.; Gallegos, R.; Schaefer, F.; Pruess, D. L. Tetrahedron, 1996, 52, 1149.
12. (c) Williams, R. M.; Yuan, C. J. Org. Chem. 1994, 57, 6190.
13. (d) Williams, R. M.; Yuan, C. J. Org. Chem. 1992, 57, 6519.
14. (e) Williams, R. M.; Im, M.-N.; Cao, J. J. Am. Chem. Soc. 1991, 113, 6976.
15. (a) Tanaka, K.; Swanishi, H. Tetrahedron: Asymmetry 1998, 9, 71.
16. (b) Bull, S. D.; Chernega, A. N.; Davies, S. G.; Moss, W. O.; Parkin, R. M. Tetrahedron 1998, 54, 10379.
17. (c) Andrews, M. J. I.; Tabor, A. B.; Tetrahedron Lett. 1997, 38, 3063.
18. (d) Nadin, A.; Derrer, S.; McGeary, R. P.; Goodman, J. M.; Raithby, P. R.; Holmes, A. B. J. Am. Chem. Soc. 1995, 117, 9768.
19. (e) Arakwa, Y.; Goto, T.; Kawase, K.; Yoshifuji, S. Chem. Pharm. Bull. 1995, 43, 535.
20. (f) Holcomb, R. C.; Schow, S.; Ayral-Kaloustian, S.; Powell, D. Tetrahedron Lett. 1994, 35, 7005.
21. (g) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727.
22. (g) Bold, G.; Allmendinger, T.; Herold, P.; Moesch, L.; Schar, H.-P.; Duthaler, R. O. Helv. Chim. Acta 1992, 75, 865.
23. (h) Gerhart, F.; Higgins, W.; Tardif, C.; Ducep, J.-B. J. Med. Chem. 1990, 33, 2157.
24. (a) Patte, J.-C. In Amino Acids: Biosynthesis and Genetic Regulation; Hermann, K. M., Somerville, R. L., Eds.; Adison-Wesley: Reading, MA, 1983; p 213.
25. (b) Girodeau, J.-M.; Agouridas, C.; Masson, M.; Pineau, R.; Le Gofic, F. J. Med. Chem. 1986, 29, 1023.
26. Luker, K. E.; Collier, J. L.; Kolodziej, E. W.; Marshall, G. R.; Goldman, W. E. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 2365.
27. Izumi, S. Nakahara, K.; Gotoh, T.; Hashimoto, S.; Kino, T.; Okahara, M.; Aoki, H.; Imanaka, H. J. Antbiot. 1983, 36, 566.
28. For examples of the sulfinimine-mediated asymmetric Strecker synthesis, see: (a) Davis, F. A.; Srirajan, V.; Titus, D. D. J. Org. Chem. 1999, 64, 6931. (b) Portonovo, P.; Liang, B.; Joullie, M. M. Tetrahedron: Asymmetry 1999, 10, 1451. (c) Davis, F. A.; Fanelli, D. L. J. Org. Chem. 1998, 63, 1981. (d) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y.-H. J. Org. Chem. 1996, 61, 440.
29. For examples of the sulfinimine-mediated asymmetric Strecker synthesis, see: (a) Davis, F. A.; Srirajan, V.; Titus, D. D. J. Org. Chem. 1999, 64, 6931. (b) Portonovo, P.; Liang, B.; Joullie, M. M. Tetrahedron: Asymmetry 1999, 10, 1451. (c) Davis, F. A.; Fanelli, D. L. J. Org. Chem. 1998, 63, 1981. (d) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y.-H. J. Org. Chem. 1996, 61, 440.
30. For examples of the sulfinimine-mediated asymmetric Strecker synthesis, see: (a) Davis, F. A.; Srirajan, V.; Titus, D. D. J. Org. Chem. 1999, 64, 6931. (b) Portonovo, P.; Liang, B.; Joullie, M. M. Tetrahedron: Asymmetry 1999, 10, 1451. (c) Davis, F. A.; Fanelli, D. L. J. Org. Chem. 1998, 63, 1981. (d) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y.-H. J. Org. Chem. 1996, 61, 440.
31. For examples of the sulfinimine-mediated asymmetric Strecker synthesis, see: (a) Davis, F. A.; Srirajan, V.; Titus, D. D. J. Org. Chem. 1999, 64, 6931. (b) Portonovo, P.; Liang, B.; Joullie, M. M. Tetrahedron: Asymmetry 1999, 10, 1451. (c) Davis, F. A.; Fanelli, D. L. J. Org. Chem. 1998, 63, 1981. (d) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y.-H. J. Org. Chem. 1996, 61, 440.
32. Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1043.
33. Borjesson, L.; Csoregh, I.; Welch, C. J. J. Org. Chem. 1995, 60, 2989.
34. (a) Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1988, 53, 2367.
35. (b) Haskell, B. E.; Bowlus, S. B. J. Org. Chem. 1976, 41, 159.
36. 1H (500 MHz) NMR.
37. For leading references to sulfinimine (N-sulfinyl imine) chemistry, see: Davis, F. A.; Andemichael, Y. M. J. Org. Chem. 1999, 64, 8627.
38. For reviews on the chemistry of sulfinimines, see: (a) Hua, D. H.; Chen, Y.; Millward, G. S. Sulfur Rep. 1999, 21, 211.
39. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.