Synthetic Studies Towards Phorboxazole B: Stereoselective Synthesis of the C3-C19 Bis-oxane Oxazole Fragment

Synlett

Volumn , Issue 12, 2003, Pages 1817-1821

  Zhang, Dong Hui ^a   Zhou, Wei Shan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Enantioselective synthesis; Mukaiyama reaction; Phorboxazole; Reduction; Williamson reaction

Indexed keywords

ALKANE DERIVATIVE; OXAZOLE DERIVATIVE; PHORBOXAZOLE B;

ALDOL REACTION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MOLECULAR DYNAMICS; REDUCTION; STEREOCHEMISTRY; WILLIAMSON REACTION;

EID: 0142123945     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41462     Document Type: Article

References (55)

1. Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126.
2. (a) Molinski, T. F.; Antonio, J. J. Nat. Prod. 1993, 56, 54.
3. (b) Molinski, T. F. Tetrahedron Lett. 1998, 37, 7879.
4. (c) Searle, P. A.; Molinski, T. F.; Brzeainski, L. J.; Leahy, J. W. J. Am. Chem. Soc. 1996, 118, 9422.
5. (a) Lee, C. S.; Forsyth, C. J. Tetrahedron Lett. 1996, 37, 6449.
6. (b) Cink, R. D.; Forsyth, C. J. J. Org. Chem. 1997, 62, 5672.
7. (c) Pattenden, G.; Plowright, A. T.; Tornos, J. A.; Ye, T. Tetrahedron Lett. 1998, 39, 6099.
8. (d) Ahmed, F.; Forsyth, C. J. Tetrahedron Lett. 1998, 39, 183.
9. (e) Ye, T.; Pattenden, G. Tetrahedron Lett. 1998, 39, 319.
10. (f) Paterson, I.; Arnott, E. A. Tetrahedron Lett. 1998, 39, 7185.
11. (g) Williams, D. R.; Clark, M. P.; Berliner, M. A. Tetrahedron Lett. 1999, 40, 2287.
12. (h) Williams, D. R.; Clark, M. P. Tetrahedron Lett. 1999, 40, 2291.
13. (i) Wolbers, P.; Misske, A. M.; Hoffmann, H. M. R. Tetrahedron Lett. 1999, 40, 4527.
14. (j) Wolbers, P.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 1905.
15. (k) Misske, A. M.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 4315.
16. (l) Wolbers, P.; Hoffmann, H. M. R. Synthesis 1999, 2291.
17. (m) Evans, D. A.; Cee, V. J.; Smith, T. E.; Santiaga, K. J. Org. Lett. 1999, 1, 87.
18. (n) Smith, A. B. III; Verhoest, P. R.; Minbiole, K. P.; Lim, J. J. Org. Lett. 1999, 1, 909.
19. (o) Smith, A. B.; Minbiole, K. P.; Verhoest, P. R.; Beauchamp, T. J. Org. Lett. 1999, 1, 913.
20. (p) Wolbers, P.; Hoffmann, H. M. R.; Sasse, F. Synlett 1999, 1808.
21. (q) Pattenden, G.; Plowright, A. T. Tetrahedron Lett. 2000, 41, 983.
22. (r) Greer, P. B.; Donaldson, W. A. Tetrahedron Lett. 2000, 41, 3801.
23. (s) Rychnovsky, S. D.; Thomas, C. R. Org. Lett. 2000, 2, 1217.
24. (t) Williams, D. R.; Clark, M. P.; Emde, V.; Berliner, M. A. Org. Lett. 2000, 2, 3023.
25. (u) Schaus, J. V.; Panek, J. S. Org. Lett. 2000, 2, 469.
26. (v) Evans, D. A.; Cee, V. J.; Smith, T. E.; Fitch, D. M.; Cho, P. S. Angew. Chem. Int. Ed. 2000, 39, 2533.
27. (w) Evans, D. A.; Fitch, D. M. Angew. Chem. Int. Ed. 2000, 39, 2536.
28. (x) Huang, H.; Panek, J. S. Org. Lett. 2001, 3, 1693.
29. (y) White, J. D.; Kranemann, C. L.; Kuntiyong, P. Org. Lett. 2001, 3, 4003.
30. (z) Greer, P. B.; Donaldson, W. A. Tetrahedron 2002, 58, 6009.
31. (a) Paterson, I.; Luckhurst, C. A. Tetrahedron Lett. 2003, 44, 3749.
32. (b) Liu, B.; Zhou, W.-S. Tetrahedron Lett. 2003, 44, 4933.
33. (c) Haustedt, L. O.; Hartung, I. V.; Hoffmann, H. M. R. Angew. Chem. Int. Ed. 2003, 42, 2711.
34. (a) Forsyth, C. J.; Ahmed, F.; Cink, R. D.; Lee, C. S. J. Am. Chem. Soc. 1998, 120, 5597.
35. (b) Evans, D. A.; Smith, T. E.; Cee, V. J. J. Am. Chem. Soc. 2000, 122, 10033.
36. (c) Smith, A. B.; Verhoest, P. R.; Minbiole, K. P.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 4834.
37. (d) Smith, A. B. I. I. I.; Minbiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942.
38. (e) Gonzalez, M. A.; Pattenden, G. Angew. Chem. Int. Ed. 2003, 42, 1255.
39. (f) Williams, D. R.; Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A.; Reeves, J. T. Angew. Chem. Int. Ed. 2003, 42, 1258.
40. (a) The methyl ketone 15 was conveniently prepared from 1-(tert-butyl-diphenyl-silanyloxy)-hex-5-en-3R-ol, see: Smith, A. B. III; Lin, Q.; Nakayama, K.; Boldi, A. M.; Brook, C. S.; McBriar, M. D.; Moser, W. H.; Sobukawa, M.; Zhuang, L. Tetrahedron Lett. 1997, 38, 8675.
41. Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226.
42. (a) Sato, M.; Kuroda, H.; Kaneko, C.; Furuya, T. J. Chem. Soc., Chem. Commun. 1994, 6, 687.
43. (b) Uesato, S.; Takeda, Y.; Hashimoto, T.; Uobe, K.; Inouye, H.; Taguchi, H.; Endo, T. Helv. Chim. Acta 1984, 67, 2111.
44. For a review on Wacker oxidation, see: Tsuji, J. Synthesis 1984, 369.
45. 2, -78°C, 85%), see: Panek, J. S.; Beresis, R. T. J. Org. Chem. 1996, 61, 6496.
46. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
47. Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R.; Roberts, S. M. Tetrahedron Lett. 1979, 20, 3981.
48. (a) Mukaiyama, T.; Banno, K.; Naraska, K. J. Am. Chem. Soc. 1974, 96, 7503.
49. (b) For 1,3-asymmetric induction in diastereoselective Mukaiyama aldol addition reaction, see: Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322.
50. (c) Also see: Reetz, M. T.; Jung, A. J. Am. Chem. Soc. 1983, 105, 4833.
51. The diastereoselective ratio was measured by HPLC analysis.
52. Lombardo, L. Org. Synth. 1987, 65, 81.
53. Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668.
54. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392.
55. Matsubara, S.; Sugihara, M.; Utimoto, K. Synlett 1998, 313.