Direct amino acid catalyzed asymmetric synthesis of polyketide sugars

Angewandte Chemie - International Edition

Volumn 44, Issue 9, 2005, Pages 1343-1345

  Casas, Jesús ^a   Engqvist, Magnus ^a   Ibrahem, Ismail ^a   Kaynak, Betul ^b   Córdova, Armando ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Aldehydes; Aldol reaction; Asymmetric catalysis; Carbohydrates; Hexoses

Indexed keywords

ALDEHYDES; AMINO ACIDS; CARBOHYDRATES; CATALYSIS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CATALYTIC PATHWAY; DEOXYSUGARS; POLYKETIDE SUGARS;

SUGARS;

ALDEHYDE; AMINO ACID; CARBONYL DERIVATIVE; DEOXYSUGAR; HEXOSE; POLYKETIDE; SUGAR;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL ANALYSIS; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY;

ALDEHYDES; AMINO ACIDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HEXOSES; LACTONES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; POLYKETIDE SYNTHASES; PROLINE; STEREOISOMERISM;

EID: 14844283105     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461400     Document Type: Article

References (66)

1. a) K. M. Koeller, C.-H. Wong, Nature 2001, 409, 232;
2. b) H. J. M. Gijsen, L. Qiao, W. Fitz, C.-H. Wong, Chem. Rev. 1996, 96, 443;
3. c) C.-H. Wong, G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamom, Oxford, 1994.
4. a) C. Khosla, J. Org. Chem. 2000, 65, 8127;
5. b) C. Khosla, P. B. Harbury, Nature 2001, 409, 247;
6. c) N. Wu, F. Kudo, C. Khosla, D. E. Cane, J. Am. Chem. Soc. 2000, 122, 4847;
7. d) C. N. Boddy, K. Hotta, M. L. Tse, R. E. Watts, C. Khosla, J. Am. Chem. Soc. 2004, 126, 7436, and references therein.
8. Glycochemistry: Principles, Synthesis, and Applications (Eds.: P. Wang, C. Bertozzi), Marcel Dekker, New York, 2001.
9. C. T. Walsh, Science 2004, 303, 1805.
10. K. C. Nicolaou, H. J. Mitchell, Angew. Chem. 2001, 113, 1625; Angew. Chem. Int. Ed. 2001, 40, 1576.
11. K. C. Nicolaou, H. J. Mitchell, Angew. Chem. 2001, 113, 1625; Angew. Chem. Int. Ed. 2001, 40, 1576.
12. a) D. A. Evans, E. Hu, J. S. Tedrow, Org. Lett. 2001, 3, 3133;
13. b) M. P. Sibi, J. Lu, J. Edwards, J. Org. Chem. 1997, 62, 5864;
14. c) S. G. Davies, R. L. Nicholson, A. D. Smith, Synlett 2002, 10, 1637;
15. For selected examples of the aldol reaction in assembly of triketides see: d) A. L. Wilkinson, U. Hanefeld, B. Wilkinson, P. F. Leadlay, J. Staunton, Tetrahedron Lett. 1998, 39, 9827;
16. e) J. R. Gage, D. A. Evans, Org. Synth. 1990, 68, 83;
17. f) B. C. Raimundo, C. H. Heathcock, Synlett 1995, 1213.
18. Reviews see: a) D. A. Evans, J. V. Nelson, T. Taber in Topics in Stereochemistry, Vol. 13, Wiley, New York, 1982, p. 1;
19. b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406; Angew. Chem. Int. Ed. 2000, 39, 1352;
20. b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406; Angew. Chem. Int. Ed. 2000, 39, 1352;
21. c) C. Palomo, M. Oiarbide, J. M. García, Chem. Eur. J. 2002, 8, 36;
22. For examples of direct aldol reactions catalyzed by organometallic complexes see: d) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871;
23. For examples of direct aldol reactions catalyzed by organometallic complexes see: d) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871;
24. e) N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Oshima, T. Suzuki, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2466;
25. f) B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003;
26. g) B. M. Trost, E. R. Silcoff, H. Ito, Org. Lett. 2001, 3, 2497;
27. h) D. A. Evans, J. S. Tedrow, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2002, 124, 392.
28. a) A. Heine, G. DeSantis, J. G. Luz, M. Mitchell, C.-H. Wong, I. A. Wilson, Science 2001, 294, 369;
29. b) H. J. M. Gijsen, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 8422;
30. c) H. J. M. Gijsen, C.-H. Wong, J. Am. Chem. Soc. 1995, 117, 7585;
31. d) H. J. M. Gijsen, C.-H. Wong, J. Am. Chem. Soc. 1995, 117, 2947;
32. e) J. Liu, C.-H. Wong, Angew. Chem. 2002, 114, 1462; Angew. Chem. Int. Ed. 2002, 41, 1404.
33. e) J. Liu, C.-H. Wong, Angew. Chem. 2002, 114, 1462; Angew. Chem. Int. Ed. 2002, 41, 1404.
34. a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726;
35. a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726;
36. b) B. List, Tetrahedron 2002, 58, 5573;
37. c) E. R. Jarvo, S. J. Miller, Tetrahedron 2002, 58, 2481;
38. d) R. O. Duthaler, Angew. Chem. 2003, 115, 1005; Angew. Chem. Int. Ed. 2003, 42, 975;
39. d) R. O. Duthaler, Angew. Chem. 2003, 115, 1005; Angew. Chem. Int. Ed. 2003, 42, 975;
40. e) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248; Angew. Chem. Int. Ed. 2004, 43, 5138.
41. e) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248; Angew. Chem. Int. Ed. 2004, 43, 5138.
42. a) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301;
43. b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798;
44. c) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620;
45. d) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420;
46. d) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. 2004, 116, 2474; Angew. Chem. Int. Ed. 2004, 43, 2420;
47. e) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003,115, 2474; Angew. Chem. Int. Ed. 2003, 42, 2785;
48. e) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. 2003,115, 2474; Angew. Chem. Int. Ed. 2003, 42, 2785;
49. f) N. S. Chowdari, D. B. Ramachary, A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591;
50. g) A. Córdova, Tetrahedron Lett. 2004, 45, 3949;
51. h) J. Casas, H. Sundén, A. Córdova, Tetrahedron Lett. 2004, 45, 6117;
52. i) A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152.
53. i) A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204; Angew. Chem. Int. Ed. 2004, 43, 2152.
54. a) A. Córdova, H. Sundén, M. Engqvist, I. Ibrahem, J. Casas, J. Am. Chem. Soc. 2004, 126, 3914;
55. b) A. Bøgevig, H. Sundén, A. Córdova, Angew. Chem. 2004, 116, 1129; Angew. Chem. Int. Ed. 2004, 43, 1109;
56. b) A. Bøgevig, H. Sundén, A. Córdova, Angew. Chem. 2004, 116, 1129; Angew. Chem. Int. Ed. 2004, 43, 1109;
57. c) A. Córdova, H. Sundén, A. Bøgevig, M. Johansson, F. Himo, Chem. Eur. J. 2004, 10, 3673;
58. d) A. Córdova, Chem. Eur. J. 2004, 10, 1987;
59. e) A. Córdova, Acc. Chem. Res. 2004, 37, 102;
60. f) A. Córdova, Synlett 2003, 1651, and references therein.
61. After the submission of this manuscript MacMillan and co-workers reported an excellent short synthesis of hexoses based on a proline-catalyzed dimerization of protected glycoaldehydes followed by Lewis acid mediated indirect tandem Mukaiyama aldol addition cyclization reactions. A. B. Northrup, D. W. C. MacMillan, Science 2004, 305, 1752.
62. CCDC-251202 contains the crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam. ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
63. S. Pizarello, A. L. Weber, Science 2004, 303, 1151. For a Zn/amino acid mediated sugar synthesis under prebiotic conditions see: J. Kofoed, M. Machuqueiro, J.-L. Reymond, T. Darbre, Chem. Commun. 2004, 26, 1540.
64. S. Pizarello, A. L. Weber, Science 2004, 303, 1151. For a Zn/amino acid mediated sugar synthesis under prebiotic conditions see: J. Kofoed, M. Machuqueiro, J.-L. Reymond, T. Darbre, Chem. Commun. 2004, 26, 1540.
65. a) L. E. Orgel, Science 2000, 290, 1306;
66. N. Hall, Chem. Commun. 2004, 1247, and references therein.