A new synthetic method for the preparation of α,β-didehydroamino acid derivatives by means of a wittig-type reaction. Syntheses of (2S, 4S)- and (2R, 4R)-4-hydroxyprolines

Bulletin of the Chemical Society of Japan

Volumn 75, Issue 11, 2002, Pages 2517-2525

  Kimura, Rumi ^a   Nagano, Tanemasa ^a   Kinoshita, Hideki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; DERIVATIVES;

WITTIG-TYPE REACTIONS;

AMINO ACIDS;

2 (N TERT BUTOXYCARBONYLAMINO) 4,5 ISOPROPYLIDENEDIOXY 2 PENTENOATE; ALPHA,BETA DIDEHYDROAMINO ACID DERIVATIVE; AMINO ACID DERIVATIVE; ETHYL 2 (N TERT BUTOXYCARBONYLAMINO) 4,5 ISOPROPYLIDENEDIOXY 2 PENTENOATE; ETHYL N TERT BUTOXYCARBONYL ALPHA TOSYLGLYCINATE; GLYCINE DERIVATIVE; HYDROXYPROLINE; N ALPHA TOSYLGLYCINATE; PHOSPHINE DERIVATIVE; TRIBUTYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

EID: 0036905682     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.75.2517     Document Type: Article

References (37)

1. a) T. Ueno, T. Nakashima, Y. Hayashi, and H. Fukami, Agric. Biol. Chem., 39, 1115 (1975).
2. b) R. D. Durbin, "Toxins in Plant Disease," Physiological Ecology Series, Academic Press (1981), p. 357.
3. c) M. F. Mackay, A. Van Donkelaar, and C. C. J. Culvenor, J. Chem. Soc., Chem. Commun., 1986, 1219.
4. d) E. D. de Silva, D. E. Williams, R. J. Anderson, H. Klix, C. F. B. Holmes, and T. M. Allen, Tetrahedron Lett., 33, 1561 (1992).
5. e) D. Botes, A. Tuinman, P. Wessels, C. Vilzoen, H. Kruger, D. H. Williams, S. Santikarn, R. Smith, and S. Hammond, J. Chem. Soc., Perkin, Trans. 1, 1984, 2311.
6. f) K. L. Reinhart, K. Harada, M. Namikoshi, M. H. G. Munro, J. W. Blunt, P. E. Mulligan, Y. R. Beasley, A. M. Dahlem, and W. W. Carmichael, J. Am. Chem. Soc., 110, 8557 (1988).
7. g) K. Nagaoka, M. Matsumoto, J. Oono, K. Yokoi, S. Ishizeki, and T. Nakashima, J. Antibiot., 36, 1527 (1986).
8. a) H. E. Carter, "Organic Reactions," John Wiley and Sons Inc. (1949), Vol. 3, p. 198.
9. b) I. Photaki, J. Am. Chem. Soc., 85, 1123 (1963).
10. c) D. H. Rich and J. P. Tam, J. Org. Chem., 42, 3815 (1977).
11. d) C. Shin, Y. Yonezawa, K. Unoki, and J. Yoshimura, Tetrahedron Lett., 1979, 1049.
12. e) S. Nomoto, A. Sano, and T. Shiba, Tetrahedron Lett., 1979, 521.
13. f) P. A. Manis and M. W. Rathke, J. Org. Chem., 45, 4952 (1980).
14. g) Y. Shimohigashi and G. H. Stammer, J. Chem. Soc., Perkin Trans. 1, 1983, 803.
15. h) U. Schmidt, A. Lieberknecht, and J. Wild, Synthesis, 1984, 53.
16. i) N. M. Okeley, Y. Zhu, and W. A. van der Donk, Org. Lett., 2, 3603 (2000).
17. a) W. S. Knowles, M. J. Sabacky, B. D. Vineyard, and D. J. Weinkauff, J. Am. Chem. Soc., 97, 2567 (1975).
18. b) A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, and R. Noyori, J. Am. Chem. Soc., 102, 7932 (1980).
19. c) R. Noyori, "Asymmetric Catalysis in Organic Syntheses," Wiley-interscience, New York (1994), p. 16.
20. d) E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, "Comprehensive Asymmetric Catalysis," Springer-Verlag, Berlin and Heiderberg (1999), Vol. 1, p. 145.
21. a) H. Kinoshita, H. Ngwe, K. Kohori, and K. Inomata, Chem. Lett., 1993, 1441.
22. b) T. Kakiuchi, H. Kato, K. P. Jayasundera, H. Higashi, K. Watabe, D. Sawamoto, H. Kinoshita, and K. Inomata, Chem. Lett., 1998, 1001.
23. c) T. Kakiuchi, H. Kinoshita, and K. Inomata, Synlett, 1999, 901.
24. T. Nagano and H. Kinoshita, Bull. Chem. Soc. Jpn., 73, 1605 (2000).
25. J. Jurczack, S. Pikul, and T. Bauer, Tetrahedron, 42, 447 (1986).
26. a) W. M. Lewko, L. A. Liotta, M. S. Wicha, B. K. Vonderhaar, and W. R. Kidwell Cancer Res., 41, 2855 (1981).
27. b) E. M. Tan, L. U. Ryhanen, and J. Uitto, J. Invest Delmatol., 80, 261(1983).
28. c) W. D. Klohs, R. W. Steinkampf, M. S. Wicha, A. E. Mertus, J. B. Tunas, and W. R. Leopold, J. Natl. Cancer Inst., 75, 353 (1985).
29. J. C. Sheehan, H.G. Zachau, and W.B. Lawson, J. Am. Chem. Soc., 80, 3348 (1958).
30. a) A. A. Patchett and B. Witkop, J. Am. Chem. Soc., 79, 185 (1957).
31. b) G. L. Baker, S. J. Fritschel, J. R. Stille, and J. K. Stille, J. Org. Chem., 46, 2954 (1981).
32. c) M. Seki and K. Matsumoto, Biosci. Biotech. Biochem., 59, 1161 (1995).
33. a) C. Eguchi and A. Kakuta, Bull. Chem. Soc. Jpn., 47, 1704 (1974).
34. b) K. Burger, M. Rudolph, and S. Fehn, Angew. Chem., Int. Ed. Engl., 32, 285 (1993).
35. L. A. Paquette, "Encyclopedia for Reagent of Organic Syntheses," John Wiley & Sons, New York (1995), Vol. 8, p. 5379.
36. A. Neuberger, J. Chem. Soc., 1945, 429.
37. K. Feichtinger, H. L. Sings, T. J. Baker, K. Matthews, and M. Goodman, J. Org. Chem., 63, 8432 (1998).