Total synthesis of (-)-kendomycin

Organic Letters

Volumn 10, Issue 17, 2008, Pages 3813-3816

  Lowe, Jason T ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; IODIDE; KENDOMYCIN; RIFABUTIN; SAMARIUM; SAMARIUM DIIODIDE;

ARTICLE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; IODIDES; RIFABUTIN; SAMARIUM; STEREOISOMERISM;

EID: 55949096831     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801499s     Document Type: Article

References (52)

1. (a) Funahashi, Y.; Kawamura, N.; Ishimaru, T. Japan Patent 08231551 [A2960910], 1996; Chem. Abstr. 1997, 126, 6553.
2. (b) Funahashi, Y.; Kawamura, N.; Ishimaru, T. Japan Patent 08231552, 1996; Chem. Abstr. 1996, 125, 326518.
3. Su, M. H.; Hosken, M. I.; Hotovec, B. J.; Johnston, T. L. U.S. Patent 5728727 [A 980317], 1998; Chem. Abstr. 1998, 128, 239489.
4. (a) Bode, H. B.; Zeeck, A. J. Chem. Soc., Perkin Trans. 1 2000, n/a, 323-328.
5. (b) Bode, H. B.; Zeeck, A. J. Chem. Soc., Perkin Trans. 1 2000, n/a, 2665-2670.
6. Elnakady, Y. A.; Rohde, M.; Sasse, F.; Backes, C.; Keller, A.; Lenhof, H. P.; Weissman, K. J.; Mueller, R. ChemBioChem. 2007, 8, 1261-1272.
7. Yuan, Y.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004, 126, 14720-14721.
8. (a) Smith, A. B., III; Mesaros, E. F.; Meyer, E. A. J. Am. Chem. Soc. 2005, 127, 6948-6949.
9. (b) Smith, A. B., III; Mesaros, E. F.; Meyer, E. A. J. Am. Chem. Soc. 2006, 128, 5292-5299.
10. (a) Sengoku, T.; Uemura, D.; Arimoto, H. Chem. Lett. 2007, 36, 726-727.
11. (b) Williams, D. R.; Shamim, K. Org. Lett. 2005, 7, 4161-4164.
12. (c) White, J. D.; Smits, H. Org. Lett. 2005, 7, 235-238.
13. (d) Mulzer, J.; Pichlmair, S.; Green, M. P.; Marques, M. M. B.; Martin, H. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11980-11985.
14. (e) Sengoku, T.; Arimoto, H.; Uemura, D. Chem. Commun. 2004, n/a, 1220-1221.
15. (f) Pichlmair, S.; Marques, M. M. B.; Green, M. P.; Martin, H. J.; Mulzer, J. Org. Lett. 2003, 5, 4657-4659.
16. (g) Marques, M. M. B.; Pichlmair, S.; Martin, H. J.; Mulzer, J. Synthesis 2002, n/a, 2766-2770.
17. (h) Martin, H. J.; Drescher, M.; Kählig, H.; Schneider, S.; Mulzer, J. Angew. Chem., Int. Ed. 2001, 40, 3186-3188.
18. (i) Bahnck, K. B.; Rychnovsky, S. D. Chem. Commun. 2006, n/a, 2388-2390.
19. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
20. (a) Nicolaou, K. C.; Rao, P. B.; Hao, J.; Reddy, M. V.; Rassias, G.; Huang, X.; Chen, D. Y.-K.; Snyder, S. A. Angew. Chem., Int. Ed. 2003, 42, 1753-1758.
21. (b) Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709.
22. Fujita, K.; Mori, K. Biosci. Biotechnol. Biochem. 2001, 65, 1429-1433.
23. Gaeta, F. C. A.; Lehman de Gaeta, L. S.; Kogan, T. P.; Or, Y. S.; Foster, C.; Czarniecki, M. J. Med. Chem. 1990, 33, 964-972.
24. For recent examples of allyl and crotylsilane reagents utilized in natural product synthesis see: (a) Lowe, J. T.; Panek, J. S. Org. Lett. 2005, 7, 3231-3234.
25. (b) Su, Q.; Panek, J. S. Angew. Chem., Int. Ed. 2005, 44, 1223-1225.
26. (c) Su, Q; Panek, J. S. J. Am. Chem. Soc. 2004, 126, 2425-2430.
27. (d) Huang, H.; Panek, J. S. Org. Lett. 2003, 5, 1991-1993.
28. (a) Lowe, J. T.; Panek, J. S. Org. Lett. 2005, 7, 1529-1532.
29. (b) Lowe, J. T.; Panek, J. S. Org. Lett. 2007, 9, 2753-2753.
30. Obtained in two steps starting from commercial 2,6-dimethoxy-toluene: (a) Knolker, H.-J.; Frohner, W.; Reddy, K. R. Synthesis 2002, 4, 557-564.
31. Magnus, P.; Matthews, K. S.; Lynch, V. Org. Lett. 2003, 5, 2181-2184.
32. Nakahara, S.; Kubo, A. Heterocycles 2003, 60, 2717-2725.
33. The C7 epimer (or isomeric mixture) of 12 could be oxidized under Swern conditions to provide an intermediate ketopyran, which was selectively reduced under Luche conditions (99%, 15:1 β:α.) to provide 12 in 50% yield over three steps. See Supporting Information for details.
34. Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511.
35. Friestad, G. K.; Marie, J. C.; Deveau, A. M. Org. Lett. 2004, 6, 3249-3252.
36. Or Marshall, J. A.; Grote, J.; Audia, J. E. J. Am. Chem. Soc. 1987, 109, 1186-1194.
37. Myers, A.; Yang, B.; Kopecky, D. Tetrahedron Lett. 1996, 37, 3623-3626.
38. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
39. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769-3772.
40. Stamos, D. P.; Taylor, A. G.; Kishi, Y. Tetrahedron Lett. 1996, 37, 8647-8650.
41. (a) Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298-3299.
42. (b) For a recent example, see: Organ, M. G.; Wang, J. J. Org. Chem. 2003, 68, 5568-5574, and references therein.
43. Kim, S.; Kee, I. S.; Park, Y. H.; Park, J. H. Synlett 1991, n/a, 183-184.
44. Kim, H. M.; Sendzik, M.; Spencer, J. R.; Zhang, P. PCT Int. Appl. 2005, 117 pp. WO 2005-US18504 20050526.
45. Freshly prepared in THF from samarium and diiodoethane, see Supporting Information for details.
46. Several attempts to determine the stereochemistry through the use of chiral derivatizing agents and NMR were unsuccessful.
47. (a) Li, C.; Johnson, R. P.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 5095-5106.
48. (b) For selective deprotection review see: Crouch, R. D. Tetrahedron 2004, 60, 5833-5871.
49. (a) Ozanne, A.; Pouységu, L.; Depernet, D.; François, B.; Quideau, S. Org. Lett. 2003, 5, 2903-2906.
50. (b) Magdziak, D.; Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. Org. Lett. 2002, 4, 285-288.
51. A second Michael-type addition of water to C20a carbon of II could provide a β-hydroxy alcohol, which upon loss of water and hemiketalization would also provide kendomycin. See reference 3a for details.
52. Ling, T.; Poupon, E.; Rueden, E. J.; Theodorakis, E. A. Org. Lett. 2002, 4, 819-822.