Stereocontrolled synthesis of polyketide libraries: Boron-mediated aldol reactions with aldehydes on solid support

Tetrahedron

Volumn 54, Issue 49, 1998, Pages 14999-15016

  Gennari, Cesare ^a   Ceccarelli, Simona ^a   Piarulli, Umberto ^a   Aboutayab, Karim ^a   Donghi, Monica ^b   Paterson, Ian ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 (BENZYLOXY) 2,4 DIMETHYLOCTAN 3,5,8 TRIOL; 4 HYDROXYBUTYRALDEHYDE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; BORON; ENOL DICYCLOHEXYLBORINATE; LIGAND; POLYKETIDE; THIOESTER; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DIASTEREOISOMER; ORGANIC CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032480925     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00940-5     Document Type: Article

References (74)

1. 1. (a) Früchiel, J. S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17.
2. (b) Hermken, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
3. (c) Hermken, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1997, 53, 5643.
4. 2. For recent reports concerning stereoselective reactions on solid support, see: (a) Burgess, K.; Lim, D. Chem. Commun, 1997, 785.
5. (b) Moon, H. S.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088.
6. (c) Moon, H. S.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915.
7. (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023.
8. (e) Panek, J. S.; Zhu, B. J. Am. Chem. Soc. 1997, 119, 12022.
9. (f) Chen, S.; Janda, K. D. J. Am. Chem. Soc. 1997, 119, 8724.
10. (g) Wipf. P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1586.
11. (h) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature, 1997, 387, 268.
12. (i) Cernerud, M.; Reina, J. A.; Tegenfeldt, J.; Moberg, C. Tetrahedron: Asymmetry 1996, 7 , 2863.
13. (j) Thompson, L. A.; Moore, F. L.; Moon. Y.-C.; Ellman, J. A. J. Org. Chem. 1998, 63, 2066.
14. 3. (a) Staunton, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1302.
15. (b) Robinson, J. A. in Progress in Natural Product Chemistry; vol 58, pp 1-81;
16. Herz, W.; Kirby, G. W.; Steglich, W.; Tamm, C.; Eds.; Springer-Verlag, Wien, New York, 1991.
17. (c) Cane, D. E. Science 1994, 263, 338.
18. 4. (a) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809.
19. (b) Kobayashi, S.; Hachiya, I.; Masaru Y. Tetrahedron Lett. 1996, 37, 5569.
20. (c) Kurth, M. J.; Ahlberg Randall, L. A.; Chen, C.; Melander, C.; Miller, R. B.; McAlister, K.; Reitz, G.; Kang, R.; Nakatsu, T.; Green, C. J. Org. Chem. 1994, 59, 5862.
21. 5. (a) Purandare, A. V.; Natarjan, S. Tetrahedron Lett. 1997, 38, 8777.
22. (b) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655.
23. 6. (a) Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 37, 6851.
24. (b) Reggelin, M.; Brenig, V.; Welcker, R. Tetrahedron Lett. 1998, 39, 4801.
25. 7. Hoffmann, R. W. Angew. Chem. Int. Ed. Engl. 1987, 26, 489.
26. 8. (a) Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173.
27. (b) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618.
28. (c) Bernardi, A.; Comotti, A.; Gennari, C.; Hewkin, C. T.; Goodman, J. M.; Schlapbach, A.; Paterson, I. Tetrahedron 1994, 50, 1227.
29. (d) Gennari, C.; Vulpetti, A.; Moresca, D.; Pain, G. Tetrahedron Lett. 1994, 35, 4623.
30. (e) Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
31. (f) Gennari, C.; Moresca, D.; Vulpetti, A.; Pain, G. Tetrahedron 1997, 53, 5593.
32. (g) Gennari, C.; Vulpetti, A.; Moresca, D. Tetrahedron Lett. 1994, 35, 4857.
33. (h) Gennari, C.; Vulpelti, A.; Pain, G. Tetrahedron 1997, 53, 5909.
34. (i) Gennari, C.; Pain, G. Tetrahedron Lett. 1996, 37, 3747.
35. (j) Gennari, C.; Mongelli, N.; Vanotti, E.; Vulpetti, A. British Patent - Application N. 95/12,471.5, Filed June 20, 1995; PCT Int. Appl. EP 96 - 02409, June 4 1996; WO 97 00,870, Jan 9 1997.
36. (k) Gennari, C.; Donghi, M.; Mongelli, N.; Vanotti, E.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1723.
37. (l) Gennari, C.; Carcano, M.; Donghi, M.; Mongelli, N.; Vanotti, E.; Vulpetti, A. J. Org. Chem. 1997, 62, 4746. For reviews, see:
38. (m) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613.
39. (n) Gennari, C. Pure Appl. Chem. 1997, 69, 507.
40. 9. (a) Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedron Lett. 1989, 30, 7121.
41. (b) Paterson, I; Perkins, M. V. J. Am. Chem. Soc. 1993, 115, 1608.
42. (c) Paterson, I.; Tillyer, R. D.; Ryan, G. R. Tetrahedron Lett. 1993, 34, 4389.
43. (d) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182.
44. (e) Paterson, I.; Yeung, K.-S. Tetrahedron Lett. 1993, 34, 5347.
45. (f) Paterson, I.; Wren, S. P. J. Chem. Soc., Chem. Commun. 1993, 1790.
46. (g) Paterson, I.; Norcross, R. D.; Ward, R. A.; Romea, P.; Lister, M. A. J. Am. Chem. Soc. 1994, 116, 11287.
47. (h) Paterson, I.; Schlapbach, A. Synlett 1995, 498.
48. (i) Paterson, I.; Cumming, J. G.; Ward, R. A.; Lamboley, S. Tetrahedron 1995, 51, 9393.
49. (j) Paterson, I.; Nowak, T. Tetrahedron Lett. 1996, 37, 8243.
50. (k) Paterson, I.; Feßner, K.; Finlay, M. R. V.; Jacobs, M. F. Tetrahedron Lett. 1996, 37, 8803.
51. (l) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
52. (m) Paterson, I.; Keown, L. E. Tetrahedron Lett. 1997, 38, 5727.
53. (n) Paterson, I.; Cowden, C. J.; Woodrow, M. D. Tetrahedron Lett. 1998, 39, 6037. For reviews, see:
54. (o) Paterson, I. Pure Appl. Chem. 1992, 64, 1821.
55. (p) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
56. 10. Paterson, I.; Scott, J. P. Tetrahedron Lett. 1997, 38, 7441.
57. 11. Kurth, M. J. Chimia 1996, 50, 261.
58. 12. (a) Gennari, C.; Bernardi, A.; Cardani, S.; Scolastico, C. Tetrahedron Lett. 1985, 26, 797.
59. (b) Gennari, C.; Beretta, M. G.; Bernardi, A.; Moro, G.; Scolastico, C.; Todeschini, R. Tetrahedron 1986, 42, 893.
60. (c) Gennari, C.; Cozzi, P. G. Tetrahedron 1988,44, 5965.
61. 13. Chen, C.; Ahlberg Randall, L. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661.
62. 14. (a) Beebe, X.; Shore, N. E.; Kurth, M. J. J. Org. Chem. 1995, 60, 4196.
63. (b) Ayres, J. T.; Mann, C. K. Polym. Lett. 1965, 3, 505.
64. 15. (a) Paterson, I.; Perkins, M. V. Tetrahedron Lett. 1992, 33, 801.
65. (b) Paterson, I.; Channon, J. A. Tetrahedron Lett. 1992, 33, 797.
66. (c) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811.
67. (d) Paterson, I.; McLeod, M. D. Tetrahedron Lett. 1997, 38, 4183.
68. 16. (a) Randolph. J. T.; McClure, K. F.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5712.
69. (b) Chan, T.-H.; Huang, W.-Q. J. Chem. Soc. Chem. Commun. 1985, 909.
70. 17. (a) Rychnovsky, S. D.; Rogers, B.; Yang G. J. Org. Chem. 1993, 58, 3511.
71. (b) Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099.
72. 18. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
73. 19. Leznoff, C.C.; Wong, J.Y. Can. J. Chem. 1973, 51, 3756.
74. 20. Routledge, A.; Abell, C.; Balasubramanian, S. Synlett 1997, 61.