Novel synthesis of (+)-hydantocidin based on the plausible biosynthetic pathway

Tetrahedron

Volumn 52, Issue 4, 1996, Pages 1177-1194

  Nakajima, Noriyuki ^a   Matsumoto, Miyoko ^a   Kirihara, Masayuki ^a   Hashimoto, Masaru ^a   Katoh, Tadashi ^a   Terashima, Shiro ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

5 epi hydantocidin; D fructose; D isoascorbic acid; D psicose; herbicide; hydantocidin; intramolecular N,O spiroketal formation; one step synthesis; plausible biosynthetic pathway; urea

Indexed keywords

HYDANTOCIDIN; HYDANTOIN DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030052849     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00975-2     Document Type: Article

References (39)

1. a) Sankyo, Eur. Pat. Appl. 0232 572 A2, 19, 08, 87
2. b) Nakajima, M.; Itoi, K.; Takamatsu, Y.; Okazaki, H.; Kinoshita, T.; Shindo, M.; Kawakubo, K.; Honma, T.; Toujigamori, M.; Haneishi, T. J. Antibiot., 1991, 44, 293.
3. Ciba Geigy AG, DE pat. 4129-616-A, 10, 09, 90
4. Mitsubishi Kasei Corp., Jap. Pat. 04222589-A, 19, 21, 90.
5. For reviews see, a) Sammes, R. Topics in Antibiotic Chemistry, Vol 6; Ellis Horwood, 1982.
6. b) Townsend, L. B. Chemistry of Nucleoside and Neucleotide, Vol 1; Plenum Press, 1988.
7. Haruyama, H.; Kinoshita, T.; Nakajima, M.; Takayama, T.; Haneishi, T. J. Chem. Soc., Perkin Trans. I, 1991, 1637.
8. For structure-activity relationships of 1: a) Mio, S.; Sano, H.; Sindo, M.; Honma, T.; Sugai, S. Agric. Biol. Chem. 1991, 55, 1105
9. b) Mio, S; Sugai, S. Annu. Rep. Sankyo Res. Lab., 1991, 43, 133.
10. For total synthesis of 1: a) Mio, S.; Ichinose, R.; Goto, K.; Sugai, S. Tetrahedron, 1991, 47, 2111.
11. b) Mio, S.; Kitagawa, J.; Sugai, S. ibid., 1991, 47, 2133.
12. c) Ciba Geigy AG, DE pat. 4129-728-A, 10, 09, 90 (Chem. Abstr., 1992, 117, 8356a).
13. d) Chemla, P. Tetrahedron Lett. 1993, 34, 7391.
14. e) Harrington, P. M; Jung, M. M. ibid. 1994, 35, 5145.
15. For synthesis of the epimer of 1 (2): a) Fairbanks, A. J.; Ford, P. S.; Watkin, D. J.; Fleet, G W. J. Tetrahedron Lett., 1993, 34, 3327.
16. b) Fairbanks, A. J.; Fleet, G. W. J. Tetrahedron, 1995, 51, 3881.
17. For synthesis of the stereoisomers of 1: a) Mio, S.; Shiraishi, M.; Sugai, S.; Haruyama, H.; Sato, S. Tetrahedron, 1991, 47, 2121.
18. b) Mio, S.; Ueda, M.; Hamura, M.; Kitagawa, J.; Sugai, S. ibid. 1991, 47, 2145.
19. For synthesis of the analogs of 1: a) Burton, J. W.; Son, J. C.; Fairbank, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 6119.
20. b) Sano, H.; Mio, S.; Kitagawa, J. Tetrahedron. Asymmetry, 1994, 5, 2233.
21. c) Dondoni, A.; Scherrmann, M. -C.; Marra, A.; Delaine, J. -L. J Org. Chem. 1994, 59, 7517.
22. d) Bichard, C. J. F.; Mitchell, E. P.; Wormald, M. R.; Watson, K. A.; Johnson, L. N., Zographos, S. P.; Koutra, D. D.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 2145.
23. e) Brandstetter, T. W.; Kim, Y. -H.; Son, J. C.; Taylor, H. M.; Lilley, P. M. Q.; Watkin, D. J.; Johnson, L. N.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 2149.
24. f) Sano, H.; Mio, S.; Tsukaguchi, N.; Sugai, S. Tetrahedron, 1995, 51, 1387.
25. g) Sano H.; Sugai, S. Tetrahedron. 1995, 51, 4635.
26. h) Hannessian, S.; Sancéau, J. Y.; Chemla, P. Tetrahedron, 1995, 51, 6669.
27. For the preliminary communication, see, Matsumoto, M.; Kirihara, M.; Yoshino, T.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1993, 34, 6289.
28. For the preliminary communication, see, Nakajima, N.; Matsumoto, M.; Kirihara, M.; Hashimoto, M.; Katoh, T.; Terashima, S. Heterocycles, in press.
29. Prisbe, E. J.; Smejakal, J.; Verheyden, J. P. H.; Moffat, J. G. J. Org. Chem. 1976, 41, 1836.
30. a) Lindgren, B. O.; Nilsson, T. Acta Chem Scand. 1973, 27, 888.
31. b) Kraus, G. A.; Tashner, M. J. J. Org. Chem. 1980, 45, 1175.
32. c) Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron, 1981, 37, 2091.
33. Hirama, M.; Noda, T.; Yasuda, S.; Ito, S. J. Am. Chem. Soc. 1991, 113, 1830.
34. a) Sandler, S. R.; Karo, W.: Ureas. In Organic Functional Group Preparations, Vol. 2; Blomquist, A. T. Eds.; Academic Press: New York. 1971; pp. 134-165.
35. b) Mulzer, J.; Benz, G.: Heteroatom Manipulation. In Comprehensive Organic Synthesis, Vol. 6; Winterfeldt, E. Eds.; Pergamon Press: Oxford. 1991, pp. 301-417.
36. Speziale, A. J.; Smith, L. R. Org. Synth. 1966, 46, 16.
37. 2O).
38. tR-2, 9.9 min.
39. Crawford, T. C.; Crawford, S. A. Adv. Carbohydr. Chem. Biochem. 1980, 37, 79.