Total synthesis of Monatin

Organic Letters

Volumn 2, Issue 19, 2000, Pages 2967-2970

  Nakamura, Kozo ^a   Baker, Tracy J ^a   Goodman, Murray ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXY 4 (INDOL 3 YLMETHYL)GLUTAMIC ACID; 4-HYDROXY-4-(INDOL-3-YLMETHYL)GLUTAMIC ACID; DRUG DERIVATIVE; GLUTAMIC ACID; INDOLE DERIVATIVE; PLANT EXTRACT; SWEETENING AGENT;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; PLANT; STEREOISOMERISM; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUTAMIC ACID; INDOLES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT EXTRACTS; PLANTS; STEREOISOMERISM; SWEETENING AGENTS;

EID: 0034699283     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006246q     Document Type: Article

References (29)

1. Vleggaar, R.; Ackerman, L. G. J.; Steyn, P. S. J. Chem. Soc., Perkin. Trans. 1 1992, 22, 3095-3098.
2. (a) Holzapfel, C. W.; Bischofberger, K.; Olivier, J. Synth. Commun. 1994, 24(22), 3197-3211.
3. (b) Abushanab, E.; Arumugam, S. U.S. Patent 5,994,559, November 30, 1999.
4. (c) Holzapfel, C. W.; Olivier, J. Synth. Commun. 1993, 23(18), 2511-2526.
5. (a) Seebach, D.; Naef, R. Helv. Chim. Acta 1981, 64, 2704.
6. (b) Seebach, D.; Naef, R.; Calderari, G. Tetrahedron 1984, 40(8), 1313-1324.
7. (a) Hiwa, H.; Ogawa, T.; Yamada, K. Bull. Chem. Soc. Jpn. 1990, 63, 3707-3709.
8. (b) Boeckman, R. K., Jr.; Yoon, S. K.; Heckendorn, D. K. J. Am. Chem. Soc. 1991, 113, 9682-9684.
9. (c) Bojack, G.; Bornowski, H. Tetrahedron 1991, 47(44), 9179-9186.
10. (d) McPherson, D. W.; Knapp, F. F., Jr. J. Org. Chem. 1996, 61, 8335-8337.
11. (e) Visser, T. J.; Waarde, A. V.; Jansen, T. J. H.; Visser, G. M.; Mark, T. W. V. D.; Kraan, J.; Ensing, K.; Vaalburg, W. J. Med. Chem. 1997, 40, 117-124.
12. (a) Farines, M.; Soulier, J. Bull. Soc. Chim. Fr. 1970, 332.
13. (b) Hoye, T. R.; Peterson, B. H.; Miller, J. D. J. Org. Chem. 1987, 52, 1351.
14. (c) Pearson, W. H.; Cheng, M. J. J. Org. Chem. 1987, 52, 1353.
15. (d) Ortholand, J. Y.; Greiner, A. J. Bull. Soc. Chim. Fr. 1993, 130, 133.
16. (e) Nicos, A. P.; Shao-Po, L. J. Am. Chem. Soc. 1995, 117, 6394-6395.
17. (a) Forsyth, C. J.; Sabes, S. F.; Urbanek, R. A. J. Am. Chem. Soc. 1997, 119, 8381-8382.
18. (b) Sabes, S. F.; Urbanek, R. A.; Forsyth, C. J. J. Am. Chem. Soc. 1998, 120, 2534-2542.
19. (a) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361.
20. (b) Garner, P.; Park, J. M. Org. Synth. 1991, 70, 18.
21. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
22. (a) Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evard, G.; Durand, F. J. Org. Chem. 1991, 56, 5729.
23. (b) Muller, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1993, 34, 3289.
24. (c) D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C.-G. Tetrahedron Lett. 1994, 42, 7775.
25. (d) D'Aniello, F.; Falorni, M.; Mann, A.; Taddei, M. Tetrahedron: Asymmetry 1996, 7(4), 1217-1226.
26. The diastereomeric ratio was not established.
27. 1H NMR spectroscopy.
28. The ratio of diastereomers was approximately 4:3 as determined by HPLC.
29. The ratio of diastereomers was approximately 4:3 as determined by product yields.