11-step enantioselective synthesis of (-)-lomaiviticin aglycon

Journal of the American Chemical Society

Volumn 133, Issue 19, 2011, Pages 7260-7263

  Herzon, Seth B ^a   Lu, Liang ^a   Woo, Christina M ^a   Gholap, Shivajirao L ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUMOR ANTIBIOTICS; CHEMICAL SYNTHESIS; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; MODE OF ACTION; MONOMERIC INTERMEDIATE; NATURAL PRODUCTS; STEREO-SELECTIVE; STRUCTURAL FEATURE; SYNTHETIC ROUTES;

ANTIBIOTICS; BIOCHEMISTRY; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

LOMAIVITICIN AGLYCON; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; DIMERIZATION; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

ANTINEOPLASTIC AGENTS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 79955899426     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja200034b     Document Type: Article

References (39)

1. He, H.; Ding, W. D.; Bernan, V. S.; Richardson, A. D.; Ireland, C. M.; Greenstein, M.; Ellestad, G. A.; Carter, G. T. J. Am. Chem. Soc. 2001, 123, 5362
2. Ito, S.; Matsuya, T.; Omura, S.; Otani, M.; Nakagawa, A. J. Antibiot. 1970, 23, 315
3. Hata, T.; Omura, S.; Iwai, Y.; Nakagawa, A.; Otani, M. J. Antibiot. 1971, 24, 353
4. Omura, S.; Nakagawa, A.; Yamada, H.; Hata, T.; Furusaki, A.; Watanabe, T. Chem. Pharm. Bull. 1971, 19, 2428
5. Omura, S.; Nakagawa, A.; Yamada, H.; Hata, T.; Furusaki, A. Chem. Pharm. Bull. 1973, 21, 931
6. Seaton, P. J.; Gould, S. J. J. Antibiot. 1989, 42, 189 For a review of kinamycin biosynthesis, see: Gould, S. J. Chem. Rev. 1997, 97, 2499
7. DeBoer, T. J.; Backer, H. J. Diazomethane. Organic Syntheses; Wiley: New York, 1956; Vol. 36, p 16.
8. Laufer, R. S.; Dmitrienko, G. I. J. Am. Chem. Soc. 2002, 124, 1854
9. Zeng, W.; Ballard, T. E.; Tkachenko, A. G.; Burns, V. A.; Feldheim, D. L.; Melander, C. Bioorg. Med. Chem. Lett. 2006, 16, 5148
10. Feldman, K. S.; Eastman, K. J. J. Am. Chem. Soc. 2006, 128, 12562
11. Khdour, O.; Skibo, E. B. Org. Biomol. Chem. 2009, 7, 2140
12. For studies toward the syntheses of 1 and 2, see: Nicolaou, K. C.; Denton, R. M.; Lenzen, A.; Edmonds, D. J.; Li, A.; Milburn, R. R.; Harrison, S. T. Angew. Chem., Int. Ed. 2006, 45, 2076
13. Krygowski, E. S.; Murphy-Benenato, K.; Shair, M. D. Angew. Chem., Int. Ed. 2008, 47, 1680
14. Zhang, W.; Baranczak, A.; Sulikowski, G. A. Org. Lett. 2008, 10, 1939
15. Gholap, S. L.; Woo, C. M.; Ravikumar, P. C.; Herzon, S. B. Org. Lett. 2009, 11, 4322
16. Nicolaou, K. C.; Nold, A. L.; Li, H. Angew. Chem., Int. Ed. 2009, 48, 5860
17. Morris, W. J.; Shair, M. D. Tetrahedron Lett. 2010, 51, 4310
18. Lee, H. G.; Ahn, J. Y.; Lee, A. S.; Shair, M. D. Chem. -Eur. J. 2010, 16, 13058
19. For syntheses of various kinamycins, see: Lei, X.; Porco, J. A. J. Am. Chem. Soc. 2006, 128, 14790
20. Nicolaou, K. C.; Li, H.; Nold, A. L.; Pappo, D.; Lenzen, A. J. Am. Chem. Soc. 2007, 129, 10356
21. Woo, C. M.; Lu, L.; Gholap, S. L.; Smith, D. R.; Herzon, S. B. J. Am. Chem. Soc. 2010, 132, 2540 For synthesis of (±)-O -methyl-kinamycin C, see: Kumamoto, T.; Kitani, Y.; Tsuchiya, H.; Yamaguchi, K.; Seki, H.; Ishikawa, T. Tetrahedron 2007, 63, 5189 For studies toward the synthesis of kinamycin F (6), see: Chen, N.; Carriere, M. B.; Laufer, R. S.; Taylor, N. J.; Dmitrienko, G. I. Org. Lett. 2008, 10, 381
22. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40
23. Hawkins, E. G. E.; Large, R. J. Chem. Soc., Perkin Trans. 1974, 1, 280
24. For selected examples, see: Ito, Y.; Konoike, T.; Harada, T.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 1487
25. Baran, P. S.; DeMartino, M. P. Angew. Chem., Int. Ed. 2006, 45, 7083
26. DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 11546
27. For selected examples, see: Baciocchi, E.; Casu, A.; Ruzziconi, R. Tetrahedron Lett. 1989, 30, 3707
28. Avetta, C. T.; Konkol, L. C.; Taylor, C. N.; Dugan, K. C.; Stern, C. L.; Thomson, R. J. Org. Lett. 2008, 10, 5621
29. See Supporting Information.
30. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483
31. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011
32. Larock, R. C.; Hightower, T. R.; Kraus, G. A.; Hahn, P.; Zheng, D. Tetrahedron Lett. 1995, 36, 2423
33. Huot, R.; Brassard, P. Can. J. Chem. 1974, 52, 838
34. 1H NMR analysis of the unpurified reaction mixture against an internal standard. However, under all purification conditions that we have examined, the products 18 and 19 partially decompose. [Under optimized conditions, elution of analytically pure samples of 18 (or 19) resulted in 70% recovery.]
35. Evans, S.; Hamnett, A.; Orchard, A. F.; Lloyd, D. R. Faraday Discuss. Chem. Soc. 1972, 54, 227
36. Bryant, J. R.; Taves, J. E.; Mayer, J. M. Inorg. Chem. 2002, 41, 2769
37. The ratio of 22 and 23 varied somewhat between experiments but was consistently within the range 1.5-3:1. For example, in a separate 100 mg scale experiment, 22, 23, and 18 were obtained in 33%, 23%, and 15% yield, respectively.
38. 3OH) provided 24 in 38% yield; see Supporting Information.
39. Myers, A. G.; Fundy, M. A. M.; Lindstrom, P. A. Tetrahedron Lett. 1988, 29, 5609