Halocyclization and palladium(II)-catalyzed amidocarbonylation of unsaturated aminopolyols. Synthesis of 1,4-iminoglycitols as potential glycosidase inhibitors

Synthesis

Volumn , Issue 6, 1997, Pages 634-642

  Hümmer, Walter ^a   Dubois, Eric ^a   Gracza, Tibor ^a   Jäger, Volker ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Amidocarbonylation; Aminoalkenepolyols; Glycosidase inhibitors; Palladium(II) chloride catalysis; Polyhydroxylated pyrrolidines

Indexed keywords

AMINOCARB; CARBONYL DERIVATIVE; GLYCOSIDASE; HALOGEN; HETEROCYCLIC AMINE; PALLADIUM; POLYOL; PYRROLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ENZYME INHIBITION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0030805706     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3183     Document Type: Article

References (90)

1. (a) Part of the Ph. D. Dissertation. W. Hümmer, Würzburg 1990, post-doctoral work by T. Gracza 1991 at Würzburg and by E. Dubois 1992/1994 at Stuttgart.
2. (b) Preliminary communication of part of these results: Jäger, V.; Hummer, W. Angew. Chem. 1990, 102, 1182; Angew. Chem., Int. Ed. Engl. 1990, 29, 1171.
3. (b) Preliminary communication of part of these results: Jäger, V.; Hummer, W. Angew. Chem. 1990, 102, 1182; Angew. Chem., Int. Ed. Engl. 1990, 29, 1171.
4. (a) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319.
5. (b) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
6. (c) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182.
7. (d) Ganem, B. Acc. Chem. Res. 1996, 29, 340.
8. (e) Paulsen, H.; Sangster, I.; Heyns, K. Chem. Ber. 1967, 100, 802.
9. (f) Inouye, S.; Tsurudka, T.; Ito, T.; Niida, T. Tetrahedron 1968, 24, 2125.
10. Hettkamp, H.; Legler, G.; Bause, E. Eur. J. Biochem. 1984, 142, 85.
11. Fellows, L. E.; Bell, E. A.; Linn, D. G.; Pielkiewicz, F.; Miura, I.; Nakanishi, K. J. Chem. Soc., Chem. Commun. 1979, 977.
12. Elbein, A. D.; Legler, G.; Tlutsy, A.; McDowell, W.; Schwarz, R. Arch. Biochem. Biophys. 1984, 235, 579.
13. Fuhrmann, V.; Bause, E.; Legler, G.; Ploagh, H. Nature 1984, 307, 755.
14. Hohenschutz, L. D.; Bell, E. A.; Jewess, P. J.; Ledworthy, D. P.; Price, R. J.; Arnold, E.; Clardy, J. Phytochemistry 1981, 20, 811.
15. (a) Bashyal, B. P.; Fleet, G. W. J.; Gough, M. J.; Smith, P. W. Tetrahedron 1987, 43, 3083, and references cited therein.
16. (b) Schneider, M. J.; Ungemach, F. S.; Broquist, H. D.; Harris, T. M. Tetrahedron 1983, 39, 29.
17. Saul, R.; Chambers, J. P.; Molyneux, R. J.; Elbein, A. D. Arch. Biochem. Biophys. 1983, 221, 593.
18. Eis, M. J.; Rule, C. J.; Würzburg, B. A.; Ganem, B. Tetrahedron Lett. 1985, 26, 5397.
19. Buchanan, J. G.; Lumbard, K. W.; Sturgeon, R. J.; Thomson, D. K.; Wightman, R. H. J. Chem. Soc. Perkin Trans. 1 1990, 699.
20. Fleet, G. W. J.; Smith, P. W. Tetrahedron 1986, 42, 5685, and references cited therein.
21. Fleet, G. W. J.; Son, J.-C. Tetrahedron 1988, 44, 2637.
22. (a) Kuzsmann, J.; Kiss, L. Carbohydr. Res. 1986, 153, 45.
23. (b) Shing, T. K. M. Tetrahedron 1988, 44, 7261.
24. (c) Reitz, A. B.; Baxter, E. W. Tetrahedron Lett. 1990, 31, 6777.
25. (a) Fleet, G. W. J.; Nicholas, S. J.; Smith, P. W.; Evans, S. V.; Fellows, L. E.; Nash, R. J. Tetrahedron Lett. 1985, 26, 3127.
26. (b) Austin, G. N.; Fleet, G. W. J.; Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095.
27. (c) Kite, G. C.; Horn, J. M.; Romeo, J. R.; Fellows, L. E.; Lees, D. C.; Scofield, A. M.; Smith, N. G. Phytochemistry 1990, 29, 103.
28. (d) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849.
29. (a) Müller, R.; Leibold, T.; Pätzel, M.; Jäger, V. Angew. Chem. 1994, 106, 1305; Angew. Chem., Int. Ed. Engl. 1994, 33, 1295.
30. (a) Müller, R.; Leibold, T.; Pätzel, M.; Jäger, V. Angew. Chem. 1994, 106, 1305; Angew. Chem., Int. Ed. Engl. 1994, 33, 1295.
31. (b) Jäger, V.; Müller, R.; Leibold, T.; Hein, M.; Schwarz, M.; Fengler, M.; Jaroskova, L.; Pätzel, M.; LeRoy, P.-Y. Bull. Soc. Chim. Belg. 1994, 103, 491.
32. Wehner, V.; Jäger, V. Angew. Chem. 1990, 102, 1180; Angew. Chem., Int. Ed. Engl. 1990, 29, 1169.
33. Wehner, V.; Jäger, V. Angew. Chem. 1990, 102, 1180; Angew. Chem., Int. Ed. Engl. 1990, 29, 1169.
34. (a) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922.
35. (b) Häfele, B.; Schröter, D.; Jäger, V. Angew. Chem. 1986, 98, 89; Angew. Chem., Int. Ed. 1986, 25, 87.
36. (b) Häfele, B.; Schröter, D.; Jäger, V. Angew. Chem. 1986, 98, 89; Angew. Chem., Int. Ed. 1986, 25, 87.
37. (c) Koppenhoefer, B.; Walser, M.; Schröter, D.; Häfele, B.; Jäger, V. Tetrahedron 1987, 43, 2059.
38. (d) Jäger, V.; Schröter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195.
39. (a) Hümmer, W.; Gracza, T.; Jäger, V. Tetrahedron Lett. 1989, 30, 1517.
40. (b) Jäger, V.; Hümmer, W.; Stahl, U.; Gracza, T. Synthesis 1991, 769.
41. (c) Kirschbaum, B.; Stahl, U.; Jäger, V. Bull. Soc. Chim. Belg. 1994, 103, 424.
42. (d) Kirschbaum, B. Ph. D. Dissertation, Stuttgart 1996.
43. (e) cf. related routes from divinylcarbinol: Shi, Z.-c.; Lin, G.-q. Tetrahedron: Asymmetry 1995, 6, 2907; and references cited therein.
44. Reviews on electrophilic heterocyclizations: (a) Tamaru, Y.; Kawamura, S.; Bando, T.; Tanaka, K.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5491. (b) Kim, J. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721. (c) Bartlett, P. A. In Asymmetric Synthesis: Morrison, J. D. Ed., Academic Press: New York, 1984; Vol. 3. p411. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Cardillo, G.; Orena, M. In Houben-Weyl, Methoden der Organischen Chemie, Stereoselective Synthesis; Helmchen, G.; Hofmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme Verlag: Stuttgart, 1995, Vol. E21e, pp4698-4817.
45. Reviews on electrophilic heterocyclizations: (a) Tamaru, Y.; Kawamura, S.; Bando, T.; Tanaka, K.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5491. (b) Kim, J. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721. (c) Bartlett, P. A. In Asymmetric Synthesis: Morrison, J. D. Ed., Academic Press: New York, 1984; Vol. 3. p411. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Cardillo, G.; Orena, M. In Houben-Weyl, Methoden der Organischen Chemie, Stereoselective Synthesis; Helmchen, G.; Hofmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme Verlag: Stuttgart, 1995, Vol. E21e, pp4698-4817.
46. Reviews on electrophilic heterocyclizations: (a) Tamaru, Y.; Kawamura, S.; Bando, T.; Tanaka, K.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5491. (b) Kim, J. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721. (c) Bartlett, P. A. In Asymmetric Synthesis: Morrison, J. D. Ed., Academic Press: New York, 1984; Vol. 3. p411. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Cardillo, G.; Orena, M. In Houben-Weyl, Methoden der Organischen Chemie, Stereoselective Synthesis; Helmchen, G.; Hofmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme Verlag: Stuttgart, 1995, Vol. E21e, pp4698-4817.
47. Reviews on electrophilic heterocyclizations: (a) Tamaru, Y.; Kawamura, S.; Bando, T.; Tanaka, K.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5491. (b) Kim, J. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721. (c) Bartlett, P. A. In Asymmetric Synthesis: Morrison, J. D. Ed., Academic Press: New York, 1984; Vol. 3. p411. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Cardillo, G.; Orena, M. In Houben-Weyl, Methoden der Organischen Chemie, Stereoselective Synthesis; Helmchen, G.; Hofmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme Verlag: Stuttgart, 1995, Vol. E21e, pp4698-4817.
48. Reviews on electrophilic heterocyclizations: (a) Tamaru, Y.; Kawamura, S.; Bando, T.; Tanaka, K.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5491. (b) Kim, J. G.; Cha, J. K. Tetrahedron Lett. 1989, 30, 5721. (c) Bartlett, P. A. In Asymmetric Synthesis: Morrison, J. D. Ed., Academic Press: New York, 1984; Vol. 3. p411. (d) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (e) Cardillo, G.; Orena, M. In Houben-Weyl, Methoden der Organischen Chemie, Stereoselective Synthesis; Helmchen, G.; Hofmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme Verlag: Stuttgart, 1995, Vol. E21e, pp4698-4817.
49. cf. intramolecular amino- and amidomercurations: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1984, 25, 165; 1985, 26, 1123. (b) Liotta, L. J.; Bernotas, R. C.; Wilson, D. B.; Ganem, B. J. Am. Chem. Soc. 1989, 111, 785. (c) Takahata, H.; Tajima, M.; Banba, Y.; Momose, M. Chem. Pharm. Bull. 1989, 2550. (d) Shi, Z.-c.; Chun-min, Z., Lin, G.-q. Heterocycles 1995, 41, 277.
50. cf. intramolecular amino- and amidomercurations: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1984, 25, 165; 1985, 26, 1123. (b) Liotta, L. J.; Bernotas, R. C.; Wilson, D. B.; Ganem, B. J. Am. Chem. Soc. 1989, 111, 785. (c) Takahata, H.; Tajima, M.; Banba, Y.; Momose, M. Chem. Pharm. Bull. 1989, 2550. (d) Shi, Z.-c.; Chun-min, Z., Lin, G.-q. Heterocycles 1995, 41, 277.
51. cf. intramolecular amino- and amidomercurations: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1984, 25, 165; 1985, 26, 1123. (b) Liotta, L. J.; Bernotas, R. C.; Wilson, D. B.; Ganem, B. J. Am. Chem. Soc. 1989, 111, 785. (c) Takahata, H.; Tajima, M.; Banba, Y.; Momose, M. Chem. Pharm. Bull. 1989, 2550. (d) Shi, Z.-c.; Chun-min, Z., Lin, G.-q. Heterocycles 1995, 41, 277.
52. cf. intramolecular amino- and amidomercurations: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1984, 25, 165; 1985, 26, 1123. (b) Liotta, L. J.; Bernotas, R. C.; Wilson, D. B.; Ganem, B. J. Am. Chem. Soc. 1989, 111, 785. (c) Takahata, H.; Tajima, M.; Banba, Y.; Momose, M. Chem. Pharm. Bull. 1989, 2550. (d) Shi, Z.-c.; Chun-min, Z., Lin, G.-q. Heterocycles 1995, 41, 277.
53. cf. intramolecular amino- and amidomercurations: (a) Bernotas, R. C.; Ganem, B. Tetrahedron Lett. 1984, 25, 165; 1985, 26, 1123. (b) Liotta, L. J.; Bernotas, R. C.; Wilson, D. B.; Ganem, B. J. Am. Chem. Soc. 1989, 111, 785. (c) Takahata, H.; Tajima, M.; Banba, Y.; Momose, M. Chem. Pharm. Bull. 1989, 2550. (d) Shi, Z.-c.; Chun-min, Z., Lin, G.-q. Heterocycles 1995, 41, 277.
54. Peters, K.; Peters, E.-M.; von Schering, H. G.; Hümmer, W.; Jäger, V. Z. Kristallogr. 1997, 212, 171.
55. (a) Hegedus, L. S. Tetrahedron 1984, 40, 2415.
56. (b) Hegedus, L. S.; Allen, G. F.; Olsen, D. J. J. Am. Chem. Soc. 1980, 102, 3583.
57. (c) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z. J. Am. Chem. Soc. 1988, 110, 3994.
58. (d) Tamaru, Y.; Kobayashi, T.; Kawamura, S.; Ochiai, H.; Yoshida, Z. Tetrahedron Lett. 1985, 26, 4479.
59. (e) Tamaru, Y.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5731.
60. cf. related oxycarbonylation of enitols: (a) Gracza, T.; Hasenöhrl, T.; Stahl, U.; Jäger, V. Synthesis 1991, 1108. (b) Gracza, T.; Jäger, V. Synlett 1992, 191. (c) Gracza, T.; Jäger, V. Synthesis 1994, 1359, and references cited therein. (d) Review on Pd(II)-catalyzed carbonylation of unsaturated polyols and aminopolyols: Jäger, V.; Gracza, T.; Dubois, E.; Hasenöhrl, T.; Hümmer, W.; Kautz, U.; Kirschbaum, B.; Lieberknecht, A.; Remen, L.; Shaw, D.; Stahl, U.; Stephan, O. Organic Synthesis via Organometallics (OSM 5); Helmchen, G. Ed.; Proceed. 5th Symposium, Heidelberg, September 26-28, 1996, F. Vieweg & Sohn Verlagsges.: Braunschweig/Wiesbaden, in press (to appear in 1997).
61. cf. related oxycarbonylation of enitols: (a) Gracza, T.; Hasenöhrl, T.; Stahl, U.; Jäger, V. Synthesis 1991, 1108. (b) Gracza, T.; Jäger, V. Synlett 1992, 191. (c) Gracza, T.; Jäger, V. Synthesis 1994, 1359, and references cited therein. (d) Review on Pd(II)-catalyzed carbonylation of unsaturated polyols and aminopolyols: Jäger, V.; Gracza, T.; Dubois, E.; Hasenöhrl, T.; Hümmer, W.; Kautz, U.; Kirschbaum, B.; Lieberknecht, A.; Remen, L.; Shaw, D.; Stahl, U.; Stephan, O. Organic Synthesis via Organometallics (OSM 5); Helmchen, G. Ed.; Proceed. 5th Symposium, Heidelberg, September 26-28, 1996, F. Vieweg & Sohn Verlagsges.: Braunschweig/Wiesbaden, in press (to appear in 1997).
62. cf. related oxycarbonylation of enitols: (a) Gracza, T.; Hasenöhrl, T.; Stahl, U.; Jäger, V. Synthesis 1991, 1108. (b) Gracza, T.; Jäger, V. Synlett 1992, 191. (c) Gracza, T.; Jäger, V. Synthesis 1994, 1359, and references cited therein. (d) Review on Pd(II)-catalyzed carbonylation of unsaturated polyols and aminopolyols: Jäger, V.; Gracza, T.; Dubois, E.; Hasenöhrl, T.; Hümmer, W.; Kautz, U.; Kirschbaum, B.; Lieberknecht, A.; Remen, L.; Shaw, D.; Stahl, U.; Stephan, O. Organic Synthesis via Organometallics (OSM 5); Helmchen, G. Ed.; Proceed. 5th Symposium, Heidelberg, September 26-28, 1996, F. Vieweg & Sohn Verlagsges.: Braunschweig/Wiesbaden, in press (to appear in 1997).
63. cf. related oxycarbonylation of enitols: (a) Gracza, T.; Hasenöhrl, T.; Stahl, U.; Jäger, V. Synthesis 1991, 1108. (b) Gracza, T.; Jäger, V. Synlett 1992, 191. (c) Gracza, T.; Jäger, V. Synthesis 1994, 1359, and references cited therein. (d) Review on Pd(II)-catalyzed carbonylation of unsaturated polyols and aminopolyols: Jäger, V.; Gracza, T.; Dubois, E.; Hasenöhrl, T.; Hümmer, W.; Kautz, U.; Kirschbaum, B.; Lieberknecht, A.; Remen, L.; Shaw, D.; Stahl, U.; Stephan, O. Organic Synthesis via Organometallics (OSM 5); Helmchen, G. Ed.; Proceed. 5th Symposium, Heidelberg, September 26-28, 1996, F. Vieweg & Sohn Verlagsges.: Braunschweig/Wiesbaden, in press (to appear in 1997).
64. cf. related oxycarbonylation of enitols: (a) Gracza, T.; Hasenöhrl, T.; Stahl, U.; Jäger, V. Synthesis 1991, 1108. (b) Gracza, T.; Jäger, V. Synlett 1992, 191. (c) Gracza, T.; Jäger, V. Synthesis 1994, 1359, and references cited therein. (d) Review on Pd(II)-catalyzed carbonylation of unsaturated polyols and aminopolyols: Jäger, V.; Gracza, T.; Dubois, E.; Hasenöhrl, T.; Hümmer, W.; Kautz, U.; Kirschbaum, B.; Lieberknecht, A.; Remen, L.; Shaw, D.; Stahl, U.; Stephan, O. Organic Synthesis via Organometallics (OSM 5); Helmchen, G. Ed.; Proceed. 5th Symposium, Heidelberg, September 26-28, 1996, F. Vieweg & Sohn Verlagsges.: Braunschweig/Wiesbaden, in press (to appear in 1997).
65. (a) Yadav, V. K.; Rueger, H.; Benn, M. Heterocycles 1982, 19, 23; 1984, 22, 2735.
66. (a) Yadav, V. K.; Rueger, H.; Benn, M. Heterocycles 1982, 19, 23; 1984, 22, 2735.
67. (b) Buchanan, J. G.; Singh, G.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1984, 1299.
68. (a) Gurjar, M. K.; Patil, V. J.; Pawar, S. M. Indian J. Chem. Sect. B 1987, 26, 1115.
69. (b) Takahata, H.; Banba, Y.; Momose, T. Tetrahedron: Asymmetry 1991, 2, 445.
70. Fleet, G. W. J.; Karpas, A.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Peturson, S.; Namgoong, S. K.; Ramsden, N. G.; Smith, P. W.; Son, J. C. FEBS Lett. 1988, 237, 128.
71. (a) Welter, A.; Jadot, J.; Dardene, G.; Marlier, M.; Casimir, J. Phytochemistry 1976, 15, 747.
72. (b) Evans, S. V.; Fellows, L. E.; Shing, T. K. M.; Fleet, G. W. J. Phytochemistry 1985, 24, 1953.
73. Elbein, A. D.; Mitchell, M.; Sansford, B. A.; Fellows, L. E.; Evans, S. V. J. Biol. Chem. 1984, 259, 12409.
74. Chargaff, E.; Bowarnick, M. J. Biol. Chem. 1937. 118, 421.
75. Matsushima, Y.; Miyazaki, T. Bull. Chcm. Soc. Jpn. 1985, 38, 1325.
76. (a) Hanessian, S.; Ducharme, D.; Masse, R.; Capmau, M. L. Carbohydr. Res. 1978, 63, 265.
77. (b) Hanessian, S.; Ponpipom, M. M.; Lavalle, P. Carbohydr. Res. 1972, 24, 45.
78. (a) Jäger, V.; Häfele, B. Sythesis 1987, 801.
79. (b) See also Jäger, V.; Grund, H.; Schwab, W. Angew. Chem. 1979, 91, 91; Angew. Chem. Int. Ed. Engl. 1979, 18, 78.
80. (b) See also Jäger, V.; Grund, H.; Schwab, W. Angew. Chem. 1979, 91, 91; Angew. Chem. Int. Ed. Engl. 1979, 18, 78.
81. (c) cf. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990, 2400, 2411.
82. (d) Heinzer, F.; Bellus, D. Helv. Chim. Acta 1981, 64, 2279.
83. (e) Hass, W.; König, W. A. Liebigs. Ann. Chem. 1982, 1615.
84. (f) cf. Fürstner, A.; Jumbam, D.; Teslic, J.; Weidmann, H. J. Org. Chem. 1991, 56, 2213.
85. 16b
86. (a) Picasso, S.; Chen, Y.; Leibold, T.; Jäger, V.; Vogel, P. International Perspectives in Glycobiology. 2nd Oxford Int. Conf. Oxford, Great Britain, September 12-14, 1994.
87. (b) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. Soc. 1995, 60, 6806.
88. (c) Picasso, S., unpublished results, 1994.
89. (a) For a recent synthesis of 14 from tartaric acid (11 steps/48 % overall yield), see: Ryu, Y.; Kim, G. J. Org. Chem. 1995, 60, 103.
90. 36a