A synthesis of new coumarin C-glycosyl derivatives

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1715-1719

  Saha, Nabendu N ^a   Desai, Vijaya N ^a   Dhavale, Dilip D ^a  

^a UNIVERSITY OF PUNE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN DERIVATIVE; GLYCOSIDE;

CHEMICAL MODIFICATION; CHIRALITY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; NOTE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 0033525672     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981868z     Document Type: Note

References (81)

1. For recent reviews on aryl C-glycosides, see: (a) Daves, G. D., Jr. Acc. Chem. Res. 1990, 23, 201-206.
2. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
3. (c) Rahman, A. U. Studies in Natural Products Chemistry; Elsevier: Amsterdam, 1992; Vol. 10, pp 337-403.
4. (d) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20 and references therein,
5. (e) Schmidt, R. R. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
6. (f) Beau, J.-M.; Gallagher, T. Top. Curr. Chem. 1997, 187, 1-54.
7. (g) Nicotra, F. Top. Curr. Chem. 1997, 187, 55-83.
8. (g) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-717.
9. (h) Du, Y.; Linhardt, R. J. Tetrahedron 1998, 54, 9913-9959.
10. (a) Hauser, F. M.; Adams, T. C., Jr. J. Org. Chem. 1984, 49, 2296-2297.
11. (b) Nicotra, F.; Perego, R.; Ronchetti, F.; Russo, G.; Toma, L. Gazz. Chim. Ital. 1984, 114, 193-195.
12. (c) Narasaka, K.; Ichikawa, Y.-I.; Kubota, H. Chem. Lett. 1987, 2139-2142.
13. (d) Nicotra, F.; Panza, L.; Russo, G. J. Org. Chem. 1987, 52, 5627-5630.
14. (e) Wu, T.-C.; Goekjian, P. G.; Kishi, Y. J. Org. Chem. 1987, 52, 4819-4823.
15. (f) Goekjian, P. G.; Wu, T.-C.; Kang, H.-Y.; Kishi, Y. J. Org. Chem. 1987, 52, 4823-4825.
16. (g) Babirad, S. A.; Goekjian, P. G.; Kishi, Y. J. Org. Chem. 1987, 52, 4825-4827.
17. (h) Cai, M.-S.; Qui, D.-X. Carbohydr. Res. 1989, 191, 125-129.
18. (i) Gracia Martin, M. De G.; Horton, D. Carbohydr. Res. 1989, 191, 223-229.
19. (j) Matsumuto, T.; Katsuki, M..; Jona, H.; Suzuki, K. Tetrahedron. Lett. 1989, 45, 6185-6188.
20. (k) Matsumuto, T.; Hosoya, T.; Suzuki, K. Tetrahedron. Lett. 1990, 32, 4629-4632.
21. (l) Matsumoto, T.; Hosoya, T.; Suzuki, K Synlett 1991, 709-711.
22. (m) Hart, D. J.; Leroy, V.; Merriman, G. J.; Young, D. G. J. J. Org. Chem. 1992, 57, 5670-5680.
23. (n) Polt, R.; Szabo, L.; Trieiberg, J.; Li Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249-10258.
24. (o) Parker, K. A.; Koh, Y.-H. J. Am. Chem. Soc. 1994, 116, 11149-11150
25. (p) Parker, K. A.; Coburn, C. A.; Koh, Y.-H. J. Org. Chem. 1995, 60, 2938-2941.
26. (q) Mcdonald, F. E.; Zhu, H. Y. H.; Holmquist, C. R. J. Am. Chem. Soc. 1995, 117. 6605-6606.
27. (r) Furster, A.; Muller, T. J. Org. Chem. 1998, 63, 424-425.
28. (s) Crich, D.; Sun, S. J. Am. Chem. Soc. 1998, 120, 435-436.
29. (t) Douglas, N. L.; Ley, S. V.; Lucking, U.; Warriner, S. L. J. Chem. Soc., Perkin Trans. 1 1998, 51-65.
30. (u) Fiecchi, A.; Cighetti, G.; Muir, M.; Scala, A.; Tyman, J. J. Chem. Soc., Perkin Trans, 1 1998, 575-582.
31. (v) Moineau, C.; Bolitt, V.; Sinou, D. J. Org. Chem. 1998, 63, 582-591.
32. (w) Furstner, A.; Muller, T. J. Org. Chem. 1998, 63, 424-425 and references therein.
33. (x) Crich, D.; Sun, S. J. Am. Chem. Soc. 1998, 120, 435-436.
34. (y) Douglas, N. L.; Ley, S. V.; Lucking, U.; Warriner, S. L. J. Chem. Soc., Perkin Trans. 1 1998, 51-65.
35. (z) Fiecchi, A.; Cighetti, G.; Muir, M.; Scala, A.; Tyman, J. J. Chem. Soc., Perkin Trans. 1 1998, 575-582. Moineau, C.; Bolitt, V.; Sinou, D. J. Org. Chem. 1998, 63, 582-591 and references therein.
36. (z) Fiecchi, A.; Cighetti, G.; Muir, M.; Scala, A.; Tyman, J. J. Chem. Soc., Perkin Trans. 1 1998, 575-582. Moineau, C.; Bolitt, V.; Sinou, D. J. Org. Chem. 1998, 63, 582-591 and references therein.
37. (a) Kraus, G. A.; Shi, J. J. Org. Chem. 1990, 55, 4922-4925.
38. (b) Yamaguchi, M.; Horiguchi, A.; Ikeura, C.; Minami, T. J. Chem. Soc., Chem. Commun. 1992, 434-436.
39. (c) Kozikowski, A. P.; Cheng, X.-M. J. Chem. Soc., Chem. Commun. 1987, 680-683.
40. (d) Pulley, S. R.; Carey, J. P. J. Org. Chem. 1998, 63, 5275-5279.
41. (a) Dhavale, D. D.; Bhujbal, N. N.; Joshi, P.; Desai, S. G. Carbohydr. Res. 1994, 263, 303-307.
42. (b) Dhavale, D. D.; Saha, N. N.; Desai, V. N. J. Org Chem. 1991, 62, 7482-7484.
43. For references of coumarin compounds see: (a) Murray, R. D. H., Mendez, J., Brown, S. A., Eds. The Natural Coumarins, Occurrence, Chemistry and Biochemistry; John Wiley: New York, 1982.
44. (b) Murray, R. D. H. Naturally Occurring Plant Coumarins. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Steglich, W., Tamm, Ch., Eds.; Springer-Verlag: New York, 1991; Vol. 58, 83-316 and references therein.
45. (a) Baturen, D.; Batirov, E. Kh.; Malikov, V. M. Khim. Prir. Soedin. 1982, 650-651; Chem. Abstr. 1983, 98, 86226m.
46. (a) Baturen, D.; Batirov, E. Kh.; Malikov, V. M. Khim. Prir. Soedin. 1982, 650-651; Chem. Abstr. 1983, 98, 86226m.
47. (b) Hirakura, K.; Saida, I.; Fukai, T.; Nomura, T. Heterocycles 1985, 23, 2239-2242.
48. Aminov, S. D.; Vakhabov, A. A. Dokl. Akad. Nauk USSR 1985, 44-45; Chem. Abstr. 1986, 104, 122600g.
49. Aminov, S. D.; Vakhabov, A. A. Dokl. Akad. Nauk USSR 1985, 44-45; Chem. Abstr. 1986, 104, 122600g.
50. Mahling, J.-A.; Schmidt, R. R. Liebigs Ann., 1995, 467-469.
51. Jones, G. Organic Reactions; Wiley: New York, 1967; Vol. 15, pp 204-599.
52. 3, pyrrolidine, or DBU in different proportions under a variety of temperature and solvent conditions were unsuccessful. The solid-supported reactions using either silica gel or alumina or cadmium iodide also did not improve the yield. (a) Brillon, D.; Sauve, G. J. Org. Chem. 1992, 57, 1838-1842.
53. (b) Kabalka, G. W.; Pagni, R. M. Tetrahedron 1997, 53, 7999-8065 and references therein.
54. (c) Prajapati, D.; Sandhu, J. S. J. Chem. Soc., Perkin Trans. 1 1993, 739-740.
55. In 3-acyl coumarin the olefinic proton appears at δ 8.5 and the methyl at δ 2.6. (a) Dimitrova, E.; Anghelova, Y. Synth. Commun. 1986, 16(10), 1195-1205.
56. (b) Clinging, R.; Dean. F. M.; Houghton, L. E. J. Chem. Soc. C 1970, 897-902.
57. Varma, R. S.; Kabalka, G. W. Synth. Commun. 1985, 15, 985-990.
58. (a) Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567-607.
59. (b) Wigfield, D. C. Tetrahedron 1979, 35, 449-462.
60. (c) Raucher, S.; Hwang, K.-J. Synth. Commun. 1980, 10(2), 133-137.
61. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454-5459 and references therein.
62. f value of 7a than 4a; however, our attempts to isolate 7b in pure form were unsuccessful.
63. (a) Cornia, M.; Casiraghi, G. Tetrahedron 1989, 45, 2869-2874.
64. (b) Prakash, K. R. C.; Rao, S. P. Tetrahedron 1993, 49, 1505-1510.
65. (c) Hauser, F. M.; Adams, T. C. J. Org. Chem. 1984, 49, 2296-2297.
66. (d) Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640.
67. 1H NMR spectrum of 7a, the H-4 of furanose appeared at the usual value of δ 4.5, indicating the absence of the diamagnetic deshielding effect of a lactone carbonyl. Probably, the intramolecular hydrogen bonding with -OH at C-5 holds the coumarin ring as shown in conformational structure 7a.
68. (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204. Anh, N. T.; Einsenstein, O. Nouv. J. Chim. 1977, 1, 61.
69. (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204. Anh, N. T.; Einsenstein, O. Nouv. J. Chim. 1977, 1, 61.
70. (b) Marcantoni, E.; Cingolani, S.; Bartoli, G.; Bosco, M.; Sambri, L. J. Org. Chem. 1998, 63, 3624-3630.
71. (c) Conformation A has less steric impedance of the substituents than B. In addition, the nucleophilic attack in A seeks the LUMO of the carbonyl, which is stabilized through the mixing of the π* C=O orbital with the lowest energy σ* orbital associated with the electronegative oxygen of the furanose; see: Houk, K. N.; Paddon-Row: M. N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108-1117. We are thankful to one of the reviewers for his comments.
72. Debenzylation in glucofuranose derivatives require high pressure under which C=C was found to be reduced. Starting compound was recovered even after 48 h at 4 bar.
73. Lemieux, R. U.; Hendriks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056-4062.
74. 1,2 ≈ 8.2 Hz).
75. Lemieux, R. U.; Howard, J. Can. J. Chem. 1963, 41, 308-316. The characterization of structures 8-11 supported our earlier assignment for the carbinol 7a with the D-gluco configuration at C-5.
76. 1H NMR data for all these compounds and in particular for 9β thus confirms the D-gluco configuration of 7a. The H-5 appeared as a doublet with a coupling constant of ∼9.7 Hz, indicating the axial-axial relation with H-4.
77. (a) Ray, P. J. Chem. Soc. 1926, 941.
78. (b) Godfrey, J. M.; Sargent, M. V.; Eliy, J. A. J. Chem. Soc., Perkin Trans. 1 1974, 1353-1354.
79. (c) Nakazawa, K.; Matsuura, S. J. Pharm. Soc. Jpn. 1953, 73, 751; Chem. Abstr. 1954, 48, 7007a.
80. (c) Nakazawa, K.; Matsuura, S. J. Pharm. Soc. Jpn. 1953, 73, 751; Chem. Abstr. 1954, 48, 7007a.
81. 13C NMR spectra showed <5% signals corresponding to enol tautomer.