A second-generation cycloaddition route to 5-substituted 3-acyltetramic acids

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 873-876

  Jones, Raymond C F ^a   Dawson, Claire E ^a   O'Mahony, Mary J ^b  

^a OPEN UNIVERSITY   (United Kingdom)

^b Agrevo UK Ltd   (United Kingdom)

Author keywords

Acyltetramic acid; Cycloaddition; Dipole; Isoxazole; Nitrile oxide

Indexed keywords

TETRAMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033051701     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3091     Document Type: Article

References (21)

1. For a recent review and leading references, see: Royles, B. J. L. Chem. Rev. 1995, 95, 1981; Jones, R. C. F.; Begley, M. J.; Peterson, G. E.; Sumaria, S. J. Chem. Soc. Perkin Trans. I 1990, 1959.
2. For a recent review and leading references, see: Royles, B. J. L. Chem. Rev. 1995, 95, 1981; Jones, R. C. F.; Begley, M. J.; Peterson, G. E.; Sumaria, S. J. Chem. Soc. Perkin Trans. I 1990, 1959.
3. Stickings, C.E. Biochem. J, 1957, 67, 390.
4. Jones, R. C. F.; Bhalay, G.; Carter, P. A.; Duller, K. A. M.; Vulto, S. I. E. J. Chem. Soc., Perkin Trans. I 1994, 2513; Jones, R. C. F.; Bhalay, G.; Carter, P. A.; Duller, K. A. M.; Dunn, S. H. J. Chem. Soc., Perkin Trans, I 1999, in press.
5. Jones, R. C. F.; Bhalay, G.; Carter, P. A.; Duller, K. A. M.; Vulto, S. I. E. J. Chem. Soc., Perkin Trans. I 1994, 2513; Jones, R. C. F.; Bhalay, G.; Carter, P. A.; Duller, K. A. M.; Dunn, S. H. J. Chem. Soc., Perkin Trans. I 1999, in press.
6. We have to date been unable to form the required pyrrolidine enamines of γ-amino-β-ketoesters other than 4-amino-3-oxobutanoates.
7. Cf. Chung, Y. J.; Ryu, E. J.; Keum G.; Kim, B. H. Bioorg. Chem. 1996, 4, 209; Kim, B. H.; Chung, Y. J.; Ahn, H. J.; Ha, T.-K. Bull. Korean Chem. Soc. 1996, 17, 401.
8. Cf. Chung, Y. J.; Ryu, E. J.; Keum G.; Kim, B. H. Bioorg. Chem. 1996, 4, 209; Kim, B. H.; Chung, Y. J.; Ahn, H. J.; Ha, T.-K. Bull. Korean Chem. Soc. 1996, 17, 401.
9. The enamine geometry is undetermined; Scheme 2 shows the E-isomer for convenience.
10. Stork, G.; McMurry, J.E. J. Am. Chem. Soc. 1967, 89, 5461.
11. +, 11%), 311, 255, 239, 211, 155, 137 and 57 (100).
12. A low yield (≤ 18%) of pyrroloisoxazolone 12b was obtained in some attempts using mixed anhydride 10b.
13. +, 8%), 179, 165, 151, 137(100), 123, 110, 95, 70 and 57. The structure was confirmed by an X-ray crystal structure determination, ref 11.
14. Crystal data for 12b and 12c (m.p. 170-171 °C from hexane: ethyl acetate) is deposited at the Cambridge Crystallographic Database.
15. UV spectroscopy indicated hydrolysis of the enaminoketone derived from 12a was complete, but acyltetramic acid 13a proved too polar to be extracted from aqueous solution.
16. For leading references to the toxicity spectrum of tenuazonic acid, see: Lebrun, M. H.; Nicolas, L.; Boutar, M.; Gaudemer, F.; Ranomenjanahary, S.; Gaudemer, A. Phytochemistry 1988, 27, 77.
17. Cf. Poncet, J.; Jouin, P.; Castro, B.; Nicolas, L.; Boutar, M.; Gaudemer, A. J. Chem. Soc., Perkin Trans. 1 1990, 611.
18. Precursor 12b was found to be a single diastereoisomer.
19. Although the 3-acetyltetramic acids 13c,d are consistent with samples reported to retain optical activity [13c: m.p. 110 °C (lit. 114-114.5 °C; Yuki, H.; Tohira, Y.; Aoki, B.; Kano, T.; Takama, S.; Yamazaki, T. Chem. Pharm. Bull. 1967, 75, 1107). 13d: m.p. 132-135 °C (lit. 133-134 °C; Schmidlin, T.; Tamm, C. Helv. Chim. Acta 1980, 63, 121)], we assume epimerisation comparable to 13b, cf. ref. 13.
20. Although the 3-acetyltetramic acids 13c,d are consistent with samples reported to retain optical activity [13c: m.p. 110 °C (lit. 114-114.5 °C; Yuki, H.; Tohira, Y.; Aoki, B.; Kano, T.; Takama, S.; Yamazaki, T. Chem. Pharm. Bull. 1967, 75, 1107). 13d: m.p. 132-135 °C (lit. 133-134 °C; Schmidlin, T.; Tamm, C. Helv. Chim. Acta 1980, 63, 121)], we assume epimerisation comparable to 13b, cf. ref. 13.
21. Attempted acidic hydrolysis of the enaminoketone formed from 12b was unsuccessful.