Concise syntheses of (+)-macrosphelides A and B: Studies on the macro-ring closure strategy

Journal of Organic Chemistry

Volumn 74, Issue 2, 2009, Pages 554-561

  Paek, Seung Mann ^a   Yun, Hwayoung ^a   Kim, Nam Jung ^a   Jung, Jong Wha ^a   Chang, Dong Jo ^a   Lee, Sujin ^a   Yoo, Jakyung ^b   Park, Hyun Ju ^b   Suh, Young Ger ^b  

^a Seoul National University   (South Korea)

^b Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CONCISE SYNTHESIS; KEY FEATURES; MACROLIDE; NITRILE OXIDES; RING CLOSURES; SYNTHETIC ROUTES; WEINREB AMIDES;

AMIDES; CYANIDES; ESTERS; OLEFINS;

NITROGEN OXIDES;

ALKENE; AMIDE; CARBON; CARBONYL DERIVATIVE; ESTER; MACROLIDE; MACROSPHELIDE A; MACROSPHELIDE B; NITRILE OXIDE; UNCLASSIFIED DRUG; HETEROCYCLIC COMPOUND; NITRIC OXIDE;

ARTICLE; CHELATION; CHEMICAL STRUCTURE; CONFORMATION; CYCLOADDITION; ENERGY; REDUCTION; RING CLOSING METATHESIS; SYNTHESIS; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; NITRIC OXIDE;

EID: 60849132480     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8016692     Document Type: Article

References (50)

1. Dewick, P. M. Medicinal Natural Products, 2nd ed.; Wiley and Sons: Sussex, U.K., 2001.
2. Parenty, A.; Moreau, X.; Campagne, J.-M. Chem. Rev. 2006, 106 (3), 911-939.
3. Kang, E. J.; Lee, E. Chem. Rev. 2005, 105 (12), 4348-4378.
4. (a) Hayashi, M.; Kim, Y.-P.; Hiraoka, H.; Natori, M.; Takamatsu, S.; Kawakubo, T.; Masuma, R.; Komiyama, K.; Ōmura, S. J. Antibiot. 1995, 48, 1435-1439.
5. (b) Takamatsu, S.; Kim, Y.-P.; Hayashi, M.; Iraoka, H.; Natori, M.; Komiyama, K.; Ōmura, S. J. Antibiot. 1996, 49, 95-98.
6. (c) Numata, A.; Iritani, M.; Yamada, T.; Minoura, K.; Matsumura, E.; Yamori, T.; Tsuruo, T. Tetrahedron Lett. 1997, 38, 8215-8218.
7. (d) Yamada, T.; Iritani, M.; Doi, M.; Minoura, K.; Ito, T.; Numata, A. J. Chem. Soc., Perkin Trans. 1 2001, 3046-3053.
8. (e) Yamada, T.; Iritani, M.; Minoura, K.; Numata, A.; Kobayashi, Y.; Wang, Y.-G. J. Antibiot. 2002, 55, 147-154.
9. (a) Sunazuka, T.; Hirose, T.; Harigaya, Y.; Takamatsu, S.; Hayashi, M.; Komiyama, K.; (Ōmura, S.; Sprengeler, P. A.; Smith, A. B., III J. Am. Chem. Soc. 1997, 119, 10247-10248.
10. (b) Sunazuka, T.; Hirose, T.; Chikaraishi, N.; Harigaya, Y.; Hayashi, M.; Komiyama, K.; Sprengeler, P. A.; Smith, A. B., III; Ōmura, S. Tetrahedron 2005, 61 (15), 3789-3803.
11. Ōmura, S.; Komiyama, K. Immunosuppressants. PCT Int. Appl. WO 0147516 A1, 2001.
12. For recent examples of medicinal research on marcosphelides, see: (a) Ishihara, K.; Kawaguchi, T.; Matsuya, Y.; Sakurai, H.; Saiki, I.; Nemoto, H. Eur. J. Ore. Chem. 2004, 3973-3978.
13. (b) Matsuya, Y.; Kawaguchi, T.; Nemoto, H.; Nozaki, H.; Hamada, H. Heterocycles 2003, 59, 481-484.
14. (c) Matsuya, Y.; Kawaguchi, T.; Nemoto, H. Heterocycles 2003, 61, 39-43.
15. (d) Matsuya, Y.; Ishihara, K.; Funamori, N.; Kawaguchi, T.; Nemoto, H. Heterocycles 2003, 61, 59-63.
16. (e) Matsuya, Y.; Nemoto, H. Heterocycles 2005, 65, 1741-1749.
17. (f) Matsuya, Y.; Kawaguchi, T.; Ishihara, K.; Ahmed, K.; Zhao, Q.-L.; Kondo, T.; Nemoto, H. Org. Lett. 2006, 8, 4609-4612.
18. (g) Wang, B.-L.; Jiang, Z.-X.; You, Z.-W.; Qing, F.-L. Tetrahedron 2007, 63, 12671-12680.
19. (a) Kobayashi, Y.; Kumar, B. G.; Kurachi, T. Tetrahedron Lett. 2000, 41, 1559-1563.
20. (b) Kobayashi, Y.; Kumar, G. B.; Kurachi, T.; Acharya, H. P.; Yamazaki, T.; Kitazume, T. J. Org. Chem. 2001, 66, 2011-2018.
21. (c) Kobayashi, Y.; Acharya, H. P. Tetrahedron Lett. 2001, 42, 2817-2820.
22. (d) Kobayashi, Y.; Wang, Y.-G. Tetrahedron Lett. 2002, 43, 4381-4384.
23. (a) Ono, M.; Nakamura, H.; Konno, F.; Akita, H. Tetrahedron: Asymmetry 2000, 11, 2753-2764.
24. (b) Nakamura, H.; Ono, M.; Shiba, Y.; Akita, H. Tetrahedron: Asymmetry 2002, 13, 705-713.
25. (c) Nakamura, H.; Ono, M.; Makino, M.; Akita, H. Heterocycles 2002, 57, 327-336.
26. Sharma, G. V. M.; Mouli, C. C. Tetrahedron Lett. 2002, 43, 9159-9161.
27. (11) (a) Takahashi, T.; Kusaka, S.-i.; Doi, T.; Sunazuka, T.; Omura, S. Angew. Chem., Int. Ed. 2003, 42, 5230-5234.
28. (b) Kusaka, S.-I.; Dohi, S.; Doi, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 8857-8859.
29. (a) Matsuya, Y.; Kawaguchi, T.; Nemoto, H. Ore. Lett. 2003, 5, 2939-2941.
30. (b) Kawaguchi, T.; Funamori, N.; Matsuya, Y.; Nemoto, H. J. Org. Chem. 2004, 69, 505-509.
31. Paek, S.-M.; Seo, S.-Y.; Kim, S.-H.; Jung, J.-W.; Lee, Y.-S.; Jung, J.-K.; Suh, Y.-G. Org. Lett. 2005, 7, 3159-3162.
32. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
33. (a) Suh, Y.-G.; Seo, S.-Y.; Jung, J.-K.; Park, O.-H.; Jeon, L.-O. Tetrahedron Lett. 2001, 42, 1691-1694.
34. (b) Suh, Y.-G.; Jung, J.-K.; Seo, S.-Y.; Min, K.-H.; Shin, D.-Y.; Lee, Y.-S.; Kim, S.-H.; Park, H.-J. J. Org. Chem. 2002, 67, 4127-4137.
35. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083-9086.
36. Overman, L. E.; McCready, R. J. Tetrahedron Lett. 1982, 23, 2355-2358.
37. Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419-5422.
38. Faucher, A.-M.; Brochu, C.; Landry, S. R.; Duchesne, I.; Hantos, S.; Roy, A.; Myles, A.; Legault, C. Tetrahedron Lett. 1998, 39, 8425-8428.
39. Evans, D. A.; Rajapakse, H. A.; Chiu, A.; Stenkamp, D. Angew. Chem., Int. Ed. 2002, 41, 4573-4576.
40. Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394-2395.
41. Eh, M.; Schomburg, D.; Schicht, K.; Kalesse, M. Tetrahedron 1995, 51, 8983-8992.
42. Although Y. Kobayashi reported the synthesis of 3′, we couldn't handle that compound. This difference is thought to be derived from the highly labile character of 3′μ. See ref 8.
43. Baraldi, P. G.; Barco, A.; Benetti, S.; Manfredini, S.; Simoni, D. Synthesis 1987, 276-278.
44. (a) Asaoka, M.; Abe, M.; Mukata, T.; Takei, H. Chem. Lett. 1982, 11, 215-218.
45. (b) Kim, D.; Lee, J.; Shim, P. J.; Doi, T.; Kim, S. J. Org. Chem. 2002, 67, 772-781.
46. Maezaki, N.; Hirose, Y.; Tanaka, T. Org. Lett. 2004, 6, 2177-2180.
47. Esterification under other various conditions such as EDCI-DMAP, DCC-DMAP, or DCC-DMAP-CSA was unsuccessful.
48. Curran, D. P.; Kim, B. H.; Daugherty, J.; Heffner, T. A. Tetrahedron Lett. 1988, 29, 3555-3558.
49. Irie, O.; Fujiwara, Y.; Nemoto, H.; Shishido, K. Tetrahedron Lett. 1996, 37, 9229-9232.
50. When pure 21-β was transformed to 34, the two-step yield was 5 - 10%. This may be a result from the reluctance of 21-β to bond with N-O cleavage.