Concerning the synthesis of the tedanolide C(13)-C(23) fragment via anti-aldol reaction

Organic Letters

Volumn 10, Issue 10, 2008, Pages 2059-2062

  Dunetz, Joshua R ^a   Roush, William R ^a  

^a Scripps Florida ^*

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE; LACTONE; TEDANOLIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; KETONES; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 47049092017     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800546g     Document Type: Article

References (50)

1. Schmitz, F. J.; Gunasekera, S. P.; Yalamanchili, G.; Hossain, M, B.; van der Helm, D. J. Am. Chem. Soc. 1984, 106, 7251.
2. Fusetani, N.; Sugawara, T.; Matsunaga. S,; Hirota, H. J. Org. Chem. 1991, 56, 4971.
3. (a) Julian, L. D.; Newcom, J. S.; Roush, W. R. J. Am. Chem. Soc. 2005, 127, 6186.
4. (b) Roush, W. R.; Newcom, J. S. Org. Lett. 2002, 4, 4739.
5. (c) Roush, W. R.; Lane, G. C. Org. Lett. 1999, 1, 95.
6. (a) Ehrlich, G.; Hassfeld, J.; Eggert, U.; Kalesse, M. Chem. Eur. J. 2008,14, 2232.
7. (b) Ehrlich, G.; Hassfeld, J.; Eggert, U.; Kalesse. M. J. Am. Chem. Soc. 2006, 128, 14038.
8. (c) Hassfeld, J.; Eggert, U.; Kalesse, M. Synthesis 2005, 1183.
9. (d) Ehrlich, G.; Kalesse, M. Synlett 2005, 655.
10. (e) Hassfeld, J.; Kalesse, M. Synlett 2002, 2007.
11. (a) Smith, A. B., III; Lee, D. J. Am. Chem. Soc. 2007, 129, 10957.
12. (b) Cho, C.-G.; Kim, W.-S.; Smith, A. B., III. Org. Lett. 2005, 7, 3569.
13. (c) Smith, A. B., III; Adams, C. M.; Lodise Barbosa, S. A.; Degnan, A. P. Proc. Natl. Acad. Sci. U.S.A. 2004,101, 12042.
14. (d) Smith, A. B., III; Adams, C. M.; Lodise Barbosa, S. A.; Degnan. A. P. J. Am. Chem. Soc. 2003, 125, 350.
15. (e) Smith, A. B., III; Lodise, S. A. Org. Lett. 1999, 1, 1249.
16. (a) Jung, M. E.; Zhang, T.-h. Org. Lett. 2008, 10, 137.
17. (b) Jung, M. E.; Yoo, D. Tetrahedron Lett. 2008, 49, 816.
18. (c) Jung, M. E.; Yoo, D. Org. Lett. 2007, 9, 3543.
19. (d) Jung, M. E.; Lee, C. P. Org. Lett. 2001, 3, 333.
20. (e) Jung, M. E.; Lee, C. P. Tetrahedron Lett. 2000, 41, 9719.
21. (f) Jung, M. E.; Marquez, R. Org. Lett. 2000, 2, 1669.
22. (g) Jung, M. E.; Marquez, R. Tetrahedron Lett. 1999, 40, 3129.
23. (a) Wong, C.-M.; Loh, T.-P. Tetrahedron Lett. 2006, 47, 4485.
24. (b) Loh, T.-P.; Feng, L.-C. Tetrahedron Lett. 2001, 42, 6001.
25. (c) Loh, T.-P.; Feng, L.-C. Tetrahedron Lett. 2001, 42, 3223.
26. (a) Matsui, K.; Zheng, B.-Z.; Kusaka, S.-i.; Kuroda, M.; Yoshimoto, K.; Yamada, H.; Yonemitsu, O. Eur. J. Org. Chem. 2001, 3615.
27. (b) Zheng, B.-Z.; Yamauchi, M.; Dei, H.; Kusaka, S.-i.; Matsui, K.; Yonemitsu, O. Tetrahedron Lett. 2000, 41, 6441.
28. (c) Matsushima, T.; Nakajima, N.; Zheng, B.-Z.; Yonemitsu, O. Chem. Pharm. Bull. 2000, 48, 855.
29. (d) Zheng, B.-Z.; Maeda, H.; Mori, M.; Kusaka, S.-i.; Yonemitsu. O.; Matsushima. T.; Nakajima, N.; Uenishi, J.-i. Chem. Pharm. Bull. 1999, 47, 1288.
30. (e) Matsushima, T.; Mori, M.; Zheng, B.-Z.; Maeda, H.; Nakajima, N.; Uenishi, J.-i.; Yonemitsu, O. Chem. Pharm. Bull. 1999, 47, 308.
31. (f) Matsushima, T.; Zheng, B.-Z.; Maeda, H.; Nakajima, N.; Uenishi, J.-i.; Yonemitsu, O. Synlett 1999, 780.
32. (g) Matsushima, T.; Mori, M.; Nakajima, N.; Maeda, H.; Uenishi, J.-i.; Yonemitsu, O. Chem. Pharm. Bull. 1998, 46, 1335.
33. (h) Matsushima, T.; Horita, K.; Nakajima, N.; Yonemitsu. O. Tetrahedron Lett. 1996, 37, 385.
34. Liu, J.-F.; Abiko, A.; Pei, Z.; Buske, D. C.; Masamune, S. Tetrahedron Lett. 1998, 39, 1873.
35. Iwata, Y.; Tanino, K.; Miyashita, M. Org. Lett. 2005, 7, 2341.
36. (a) Taylor, R. E.; Hearn, B. R.; Ciavarri, J. P. Org. Lett. 2002, 4, 2953.
37. (b) Taylor, R. E.; Ciavarri, J. P.; Hearn, B. R. Tetrahedron Lett. 1998, 39, 9361.
38. (a) Nyavanandi, V. K.; Nadipalli, P.; Nanduri, S.; Naidu, A.; Iqbal, J. Tetrahedron Lett. 2007, 48, 6905.
39. (b) Nyavanandi, V. K.; Nanduri, S.; Dev, R. V.; Naidu, A.; Iqbal, J. Tetrahedron Lett. 2006, 47, 6667.
40. Julian, L. D. Studies toward the total synthesis of the tedanolides: Total synthesis of 13-deoxytedanolide. Ph.D. thesis, University of Michigan, 2005.
41. While this work was in progress, Kalesse reported experimental evidence for this hypothesis (refs 4a and 4b).
42. (a) Paterson, I.; Goodman, J. M.; Isaka, M. Tetrahedron Lett. 1989, 30, 7121.
43. (b) Mechanistic discussion: Vulpetti, A.; Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron 1993, 49, 685.
44. Prepared in analogous fashion to the known p-methoxybenzyl-protected Roche aldehyde: Organ, M. G.; Wang, J. J. Org. Chem. 2003, 68, 5568.
45. For a review, see: Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
46. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Sac. 1973, 95, 512.
47. (b) For a useful explanation and examples of Mosher ester analysis, see: Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
48. Rychnovsky, S. D.; Rogers, B. N.; Richardson. T. I. Acc. Chem. Res. 1998, 31, 9.
49. Ireland, R. E.; Norbeck, D, W. J Org. Chem. 1985, 50, 2198.
50. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.