Gram-scale synthesis of the A'B'-subunit of angelmicin B

Organic Letters

Volumn 13, Issue 24, 2011, Pages 6436-6439

  Milgram, Benjamin C ^a   Liau, Brian B ^a   Shair, Matthew D ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANGELMICIN B; ANTHRAQUINONE DERIVATIVE; LEWIS ACID; ORGANOSILICON DERIVATIVE;

ACTINOBACTERIA; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ACTINOBACTERIA; ANTHRAQUINONES; CATALYSIS; LEWIS ACIDS; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84055185261     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202728v     Document Type: Article

References (54)

1. (a) Uehara, Y.; Li, P. M.; Fukazawa, H.; Mizuno, S.; Nihei, Y.; Nishio, M.; Hanada, M.; Yamamoto, C.; Furumai, T.; Oki, T. J. Antibiot. 1993, 46, 1306-1308.
2. (b) Kajiura, T.; Furumai, T.; Igarashi, Y.; Hori, H.; Higashi, K.; Ishiyama, T.; Uramoto, M.; Uehara, Y.; Oki, T. J. Antibiot. 1998, 51, 394-401.
3. (c) Hori, H.; Kajiura, T.; Igarashi, Y.; Furumai, T.; Higashi, K.; Ishiyama, T.; Uramoto, M.; Uehara, Y.; Oki, T. J. Antibiot. 2002, 55, 46-52.
4. (d) Kajiura, T.; Furumai, T.; Igarashi, Y.; Hori, H.; Higashi, K.; Ishiyama, T.; Uramoto, M.; Uehara, Y.; Oki, T. J. Antibiot. 2002, 55, 53-60.
5. (e) Igarashi, Y.; Kajiura, T.; Furumai, T.; Hori, H.; Higashi, K.; Ishiyama, T.; Uramoto, M.; Uehara, Y.; Oki, T. J. Antibiot. 2002, 55, 61-70.
6. (f) Cho, S. I.; Fukazawa, H.; Honma, Y.; Kajiura, T.; Hori, H.; Igarashi, Y.; Furumai, T.; Oki, Y.; Uehara, Y. J. Antibiot. 2002, 55, 270-278.
7. For structural elucidation of angelmicin B, see: (a) Hori, H.; Higashi, K.; Ishiyama, T.; Uramoto, M.; Uehara, Y.; Oki, T. Tetrahedron Lett. 1996, 37, 2785-2788.
8. (b) Hori, H.; Igarashi, Y.; Kajiura, T.; Furumai, T.; Higashi, K.; Ishiyama, T.; Uramoto, M.; Uehara, Y.; Oki, T. J. Antibiot. 1998, 51, 402-417.
9. Yokoyama, A.; Okabekado, J.; Uehara, Y.; Oki, T.; Tomoyasu, S.; Tsuruoka, N.; Honma, Y. Leuk. Res. 1996, 20, 491-497.
10. For more information, see: ref 6e.
11. Romaine, I. M.; Hempel, J. E.; Shanmugam, G.; Hori, H.; Igarashi, Y.; Polavarapu, P. L.; Sulikowski, G. A. Org. Lett. 2011, 13, 4538-4541.
12. For studies towards angelmicin B or its related natural products, see: (a) Lee, C. S.; Audelo, M. Q.; Reibenpies, J.; Sulikowski, G. A. Tetrahedron 2002, 58, 4403-4409.
13. (b) Maharoof, U. S. M.; Sulikowski, G. A. Tetrahedron Lett. 2003, 44, 9021-9023.
14. (c) Kim, K.; Mahroof, S. M.; Raushel, J.; Sulikowski, G. A. Org. Lett. 2003, 5, 2777-2780.
15. (d) Narayan, S.; Roush, W. R. Org. Lett. 2004, 6, 3789-3792.
16. (e) Lambert, W. T; Roush, W. R. Org. Let. 2005, 7, 5501-5504.
17. (f) Lee, W.; Kim, K.; Sulikowski, G. A. Org. Lett. 2005, 7, 1687-1689.
18. (g) Li, J.; Todaro, L. J.; Mootoo, D. R. Org. Lett. 2008, 10, 1337-1340.
19. (h) Li, J.; Todaro, L.; Mootoo, D. R. Eur. J. Org. Chem. 2011, 6281-6287.
20. Franais, A.; Urban, D.; Beau, J. M. Angew. Chem., Int. Ed. 2007, 46, 8662-8665.
21. (a) Skaanderup, P. R.; Hyldtoft, L.; Madsen, R. Monatsh. Chem. 2002, 133, 467.
22. (b) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2016.
23. (c) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 2400-2410.
24. (d) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 2411-2431.
25. (e) Nakane, M.; Hutchinson, C. R.; Gollman, H. Tetrahedron Lett. 1980, 21, 1213-1216.
26. (f) Fürstner, A.; Jumbam, D.; Teslic, J.; Weidmann, H. J. Org. Chem. 1991, 56, 2213-2217.
27. Compound 8 was generated as a 3:1 mixture of diastereomers. See Supporting Information for more details.
28. Hyldtoft, L.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 8444-8452.
29. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 1995, 34, 2039-2041.
30. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
31. Parikh, J. P.; Doering, W. E. J. Am. Chem. Soc. 1967, 89, 5505-5507.
32. Jeroncic, L. O.; Cabal, M. P.; Danishefsky, S. J.; Shulte, G. M. J. Org. Chem. 1991, 56, 387-395.
33. Angell, E. C.; Fringuelli, F.; Pizzo, F.; Porter, B.; Taticchi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642-2649.
34. (a) Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540-4552.
35. (b) Ohkata, K.; Tamura, Y.; Shetuni, B. B.; Takagi, R.; Miyanaga, W.; Kojima, S.; Paquette, L. A. J. Am. Chem. Soc. 2004, 126, 16783-16792.
36. (c) Carreño, M. C.; González, M. P.; Houk, K. N. J. Org. Chem. 1997, 62, 9128-9137.
37. (a) Miller, R. D.; McKean, D. R. Synthesis 1979, 9, 730-732.
38. (b) Moher, E. D.; Collins, J. L.; Grieco, P. A. J. Am. Chem. Soc. 1992, 114, 2764-2765.
39. (c) Krafft, P. A.; Holton, R. A. Tetrahedron Lett. 1983, 24, 1345-1348.
40. (a) Ryu, I.; Murai, S.; Hatayama, Y.; Sonoda, N. Tetrahedron Lett. 1978, 19, 3455-3458.
41. (b) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611-3612.
42. (a) Dunn, T. B.; Ellis, J. M.; Kofink, C. C.; Manning, J. R.; Overman, L. E. Org. Lett. 2009, 11, 5658-5661.
43. (b) Vaughan, A.; Singer, R. D. Tetrahedron Lett. 1995, 36, 5683-5686.
44. (c) Lipshutz, B. H.; Sclafani, J. A.; Takanami, T. J. Am. Chem. Soc. 1998, 120, 4021-4022.
45. (d) Crump, R. A. N. C.; Fleming, I.; Urch, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 701-706.
46. (e) Tckmantel, W.; Oshima, K.; Nozaki, H. Chem. Ber. 1986, 119, 1581-1593.
47. (a) Vedejs, E. J. Am. Chem. Soc. 1974, 96, 5944-5946.
48. (b) Vedejs, E.; Larsen, S. Org. Synth. 1986, 64, 127-132 and references therein.
49. (a) Martin, C. L.; Overman, L. E.; Rohde, J. M. J. Am. Chem. Soc. 2010, 132, 4894-4906.
50. (b) Trost, B. M.; Waser, J.; Meyer, A. J. Am. Chem. Soc. 2008, 130, 16424-16434.
51. (c) Dimitrov, V.; Kostova, K.; Genov, M. Tetrahedron Lett. 1996, 37, 6787-6790.
52. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392-4398.
53. Lee, K.-s.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 2898-2900.
54. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.