Dihydroxyacetone variants in the organocatalytic construction of carbohydrates: Mimicking tagatose and fuculose aldolases

Journal of Organic Chemistry

Volumn 71, Issue 10, 2006, Pages 3822-3828

  Suri, Jeff T ^a   Mitsumori, Susumu ^a   Albertshofer, Klaus ^a   Tanaka, Fujie ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE SCAFFOLDS; DIHYDROXYACETONE VARIANTS; ORGANOCATALYTIC ALDOL REACTIONS; TAGATOSE ALDOLASE;

ALDEHYDES; CATALYSIS; ENZYMES; KETONES; REACTION KINETICS; STEREOCHEMISTRY;

CARBOHYDRATES;

1 AMINO 1 DEOXY DEXTRO LYXITOL; 2,2 DIMETHYL 1,3 DIOXAN 5 ONE; ALDEHYDE; CARBOHYDRATE DERIVATIVE; DIHYDROXYACETONE; DIOXANE DERIVATIVE; FRUCTOSE BISPHOSPHATE ALDOLASE; KETONE; LYXOSE; PROLINE; RIBOSE; RIBULOSE; TAGATOSE; UNCLASSIFIED DRUG;

ALDOL REACTION; BIOTRANSFORMATION; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; CRYSTALLIZATION; DEPROTECTION REACTION; DIASTEREOISOMER; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; REVIEW; STEREOCHEMISTRY;

ALDEHYDE-LYASES; CARBOHYDRATES; DIHYDROXYACETONE; DIOXANES; HEXOSES; MOLECULAR STRUCTURE;

EID: 33646508100     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0602017     Document Type: Review

References (94)

1. (a) Ritter R. T.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 3508-3533.
2. (b) Wong, C.-H.; Bryan, M. C.; Nyffeler, P. T.; Liu, H.; Chapman, E. Pure Appl. Chem. 2003, 75, 179-186.
3. (c) Wrodnigg, T. M.; Sprenger, F. K. Mini-Rev. Med. Chem. 2004, 4, 437-459.
4. Barchi, J. J., Jr. Curr. Pharm. Des. 2000, 6, 485-501.
5. (a) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
6. (b) Machajewski, T. D.; Wong, C.-H.; Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352-1374.
7. (c) Takayama, S.; McGarvey, G. J.; Wong, C.-H. Chem. Soc. Rev. 1997, 26, 407-415.
8. (d) Wymer, N.; Toone, E. J. Curr. Opin. Chem. Biol. 2000, 4, 110-119.
9. (e) Koeller, K. M.; Wong, C.-H. Nature 2001, 409, 232-240.
10. For reviews see: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
11. (b) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
12. (c) Allemann, C.; Gordillo, R.; Clemente, F.; Cheong, P. H.-Y.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558.
13. (d) Dalko, P. I.; Moisan, L. Angew Chem., Int. Ed. 2004, 43, 5138-5175.
14. (e) Notz, W.; Tanaka, F.; Barbas, C. F., III Acc. Chem. Res. 2004, 37, 580.
15. For recent work see: (f) Suri, J. T.; Steiner, D. D.; Barbas, C. F., III Org. Lett. 2005, 7, 3885-3888.
16. (g) Steiner, D. D.; Mase, N.; Barbas, C. F., III Angew. Chem., Int. Ed. 2005, 44, 3706-3710.
17. (h) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III Org. Lett. 2004, 6, 2507.
18. (i) Ramachary, D. B.; Barbas, C. F., III Org. Lett. 2005, 7, 1577-1580.
19. (j) Chowdari, N. S.; Barbas, C. F., III Org. Lett. 2005, 7, 867-870.
20. (k) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III Org. Lett. 2004, 6, 3541-3544.
21. For references on organocatalyzed aldol reactions see: (a) Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F., III J. Am. Chem. Soc. 2006, 128, 734-735.
22. (b) Mitsumori, S.; Zhang, H.; Cheong, P. H.-Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III J. Am. Chem. Soc. 2006, 128, 1040-1041.
23. (c) Mase, N.; Tanaka, F.; Barbas, C. F., III Angew. Chem., Int. Ed. 2004, 43, 2420.
24. (d) Mase, N.; Tanaka, F.; Barbas, C. F., III Org. Lett. 2003, 5, 4369.
25. (e) Cordova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301.
26. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III Tetrahedron Lett. 2002, 43, 9591.
27. (g) Sakthivel, K.; Notz, N.; Bui, T.; C. F. Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260.
28. (h) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395-2396.
29. (i) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386.
30. (j) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573.
31. (k) Cordova, A.; Notz, W.; Barbas, C. F. III Chem. Commun. 2002, 67, 3034.
32. (l) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
33. (m) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799.
34. (n) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620.
35. (o) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785.
36. (p) Casas, J.; Engqvist, M.; Ibrahem, I.; Kaynak, B.; Cordova, A. Angew. Chem., Int. Ed. 2005, 44, 1343.
37. (q) Hartikaa, A.; Arvidsson, P. I. Tetrahedron: Asymmetry 2004, 15, 1831.
38. (r) Torii, H.; Nakakai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986.
39. (s) Martin, H. J.; List, B. Synlett 2003, 1901.
40. (t) Kofoed, J.; Nielsen, J.; Reymond, J.-L. Bioorg. Med. Chem. Lett. 2003, 13, 2445.
41. (u) Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755.
42. (v) Berkessel, A.; Koch, B.; Lex, J. Adv. Synth. Catal. 2004, 346, 1141.
43. (w) Cobb, A. J. A.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 84.
44. (x) Hayashi, Y.; Sumiya, T.; Takahashi, J.; Gotoh, H.; Urushima, T.; Shoji; M. Angew. Chem., Int. Ed. 2006, 45, 958-961.
45. (y) Tang, Z.; Yang, Z.-H.; Chen, X.-H.; Cun, L.-F.; Mi, A.-Q. Jiang, Y.-Z.; Gong, L.-Z. J. Am. Chem. Soc. 2005, 127, 9285-9289.
46. (a) Takayama, S.; McGarvey, G. J.; Wong, C.-H. Annu. Rev. Microbiol. 1997, 51, 285-310.
47. (b) Fessner, W.-D.; Walter, C. Top. Curr. Chem. 1996, 184, 97-194.
48. (c) Fessner, W.-D. In Microbial Reagents In Organic Synthesis; Servi, S., Ed.; Kluwer Academic Publishers: Dordrecht, 1992; Vol. 381, pp 43-55.
49. (d) Henderson, I.; Sharpless, K. B.; Wong C.-H. J. Am. Chem. Soc. 1994, 116, 558-561.
50. Suri, J. T.; Ramachary, D. B.; Barbas, C. F., III Org. Lett. 2005, 7, 1383-1385.
51. (a) Enders, D.; Grondai, C. Angew Chem., Int. Ed. 2005, 44, 1210-1212.
52. (b) Ibrahem, I.; Cordova, A. Tetrahedron Lett. 2005, 46, 3363-3367.
53. (c) Attempts to reproduce published studies concerning the use of L-alanine as a catalyst for the synthesis of 2h under the conditions described by Cordova failed. Under these conditions, 2h was obtained in only 24% yield and 78% ee; see: Córdova, A.; Zou, W.; Ibrahem, I.; Reyes, E.; Engqvist, M.; Liao, W.-W. Chem. Commun. 2005, 3586-3588.
54. (d) Westermann, B.; Neuhaus, C. Angew Chem., Int. Ed. 2005, 44, 4077-4079.
55. (e) Enders, D.; Palecek, J.; Grondal, C. Chem. Commun. 2006, 655-657.
56. (f) Grondal, C.; Enders, D. Tetrahedron 2006, 62, 329-337.
57. Westermann and Neuhaus tested dihydroxyacetone phosphate as a substrate for the Mannich reaction and observed no reaction; see ref 8d.
58. (a) Hoppe, D.; Schmincke, H.;. Kleemann, H.-W. Tetrahedron 1989, 45, 687-694.
59. (b) Forbes, D. C.; Ene, D. G.; Doyle, M. P. Synthesis 1998, 879-882.
60. (c) Carman, R. M.; Handley, P. N. Aust. J. Chem. 2001, 54, 769-776.
61. (d) Enders, D.; Voith, M.; Ince, S. J. Synthesis 2002, 1775-1779.
62. Kim, K. S.; Hong, S. D. Tetrahedron Lett. 2000, 41, 5909-5913.
63. Ekeberg, D.; Morgenlie, S.; Stenstrom, Y. Carbohydr. Res. 2002, 337, 779-786.
64. Blanc-Muesser, M.; Defaye, J.; Horton, D. Carbohydr. Res. 1979, 68, 175-187.
65. The self-condensation of 1 is a competing side reaction giving acetonide protected dendroketose 12b. (Equation Presented)
66. (a) Ungm, F. M. Adv. Carbohvdr. Chem. Biochem. 1981, 38, 323.
67. (b) Iwasa, T.; Kusuka, T.; Suetomi, K. J. Antibiot. 1978, 31, 511-518.
68. (c) Harada, S.; Kishi, T. J. Antibiot. 1978, 31, 519-524.
69. (d) Harada, S.; Mizuta, E.; Kishi, T. Tetrahedron 1981, 37, 1317-1327.
70. (e) Takatsuki, A.; Arima, K.; Tamura, G. J. Antibiot. 1971, 24, 215-223.
71. (f) Takatsuki, A.; Tamura, G. J. Antibiot. 1971, 24, 224-231.
72. (g) Takatsuki, A.; Tamura, G. J. Antibiot. 1971, 24, 232-238.
73. (h) Takatsuki, A.; Kawamura, K.; Okina, M.; Kodama, Y.; Ito, T.; Tamura, G. Agric. Biol. Chem. 1977, 41, 2307-2309.
74. For references on analogues of 3-deoxy-D-manno-2-octulosonic acid, see: (i) Claesson, A.; Luthman, K.; Gustafsson, K.; Bondesson, G. Biochem. Biophys. Res. Commun. 1987, 143, 1063.
75. (j) Molin, H.; Ring, B. G. Tetrahedron Lett. 1985, 26, 617.
76. (k) Norbeck, D. W.; Kramer, J. B. Tetrahedron Lett. 1987, 28, 773.
77. (l) Norbeck, D. W.; Kramer, J. B.; Lartey, P. A. J. Org. Chem. 1987, 52, 2174.
78. (m) Tadanier, J.; Lee, C. M.; Wittern, D.; Wideburg, N. Carbohydr. Res. 1990, 201, 185.
79. (n) Tadanier, J.; Lee, C. M.; Hengeveld, J.; Rosenbrook, W., Jr.; Whittern, D.; Wideburg, N. Carbohydr. Res. 1990, 201, 209.
80. (a) Brimacombe, J. S.; Hanna, R.; Kabir, A. K. M. S. Bennett, F.; Taylor, I. D. Org. Biomol. Chem. 1986, 815-821.
81. (b) Brimacombe, J. S.; Hanna, R.; Kabir, A. K. M. S. Org. Biomol. Chem. 1986, 823-828.
82. (c) Brimacombe, J. S.; Kabir, A. K. M. S. Carhohydr. Res. 1986, 150, 35-51.
83. (d) Brimacombe, J. S.; Kabir, A. K. M. S. Carbohydr. Res. 1986, 158, 81-89.
84. Craig, D.; Pennington, M. W.; Warner, P. Tetrahedron 1999, 55, 13495-13512.
85. Bedarski, M. D.; Waldmann, H. J.; Whitesides, G. M. Tetrahedron Lett. 1986, 27, 5807.
86. Paton, R. M.; Young, A. A. Org. Biomol. Chem. 1997, 629-635.
87. (a) Torok, B.; Abid, M.; London, G.; Esquibel, J.; Torok, M.; Mhadgut, S. C.; Van, P.; Prakash, G. K. S. Angew Chem., Int. Ed. 2005, 44, 3086-3089.
88. (b) Lyle, M. P. A.; Draper, N. D.; Wilson, P. D. Org. Lett. 2005, 7, 901-904.
89. (c) Gathergood, N.; Juhl, K.; Poulsen, T. B.; Thurdrup, K.; Jorgensen, K. A. Org. Biomol. Chem. 2004, 2, 1077-1085.
90. (d) Bogevig, A.; Gothelf, K. V.; Jorgensen, K. A. Chem.-Eur. J. 2002, 8, 5652-5661.
91. (e) Prakash, G. K. S.; Van, P.; Torok, B.; Olah, G. A. Synlett 2003, 4, 527-531.
92. Baasner, B.; Hagemann, H.; Tatlow, J. C.; Eds. Organofluorine compounds. In Houben-Weyl, Methods of Organic Chemistry; Thieme-Verlag: Stuttgart, 1999/2000; Vol. E 10a-c and papers cited therein.
93. For a recent review on dihydroxyacetone derivatives, see: Enders, D.; Voith, M.; Lenzen, A. Angew Chem., Int. Ed. 2005, 44, 2-23.
94. More, J. D.; Finney, N. S. Org. Lett. 2002, 4, 3001-3003.