Synthetic study of diversifolin: The construction of 11-oxabicyclo[6.2.1] undec-3-ene core using ring-closing metathesis

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5533-5536

  Nakamura, Tomoaki ^a   Oshida, Motoko ^a   Nomura, Tomoko ^a   Nakazaki, Atsuo ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; DIVERSIFOLIN; LACTONE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

BICYCLO COMPOUNDS; CYCLIZATION; LACTONES; SESQUITERPENES;

EID: 38349171276     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7025119     Document Type: Article

References (33)

1. (a) Cicció, J. F.; Castro, V. H.; Calzada, J. G. Rev. Latinoam. Quim. 1979, 10, 134-135.
2. (b) Gao, F.; Miski, M.; Gage, D. A. G.; Mabry, T. J. J. Nat. Prod. 1985, 48, 316-318.
3. (c) Rüngeler, P.; Lyß, G.; Castro, V.; Mora, G.; Pahl, H. L.; Merfort, I. Planta Med. 1998, 64, 588-593.
4. (d) Schuster, A.; Stokes, S.; Papastergiou, F.; Castro, V.; Poveda, L.; Jakupovic, J. Phytochemistry 1992, 31, 3139-3141.
5. (a) Sarma, J. C.; Sharma, R. P.; Jong, R.; Stam, C. H. Phytochemistry 1987, 26, 2406-2407.
6. (b) Bordoloi, M.; Barua, N. C.; Ghosh, A. C. Phytochemistry 1996, 41, 557-559.
7. (c) Pereira, P. S.; Dias, D. A.; Vichnewski, W.; Nasi, A. M. T. T.; Herz, W. Phytochemistry 1997, 45, 1445-1448.
8. (d) Gu, J. Q.; Gills, J. J.; Park, E. J.; Mata-Greenwood, E.; Hawthorne, M. E.; Axelrod, F.; Chavez, P. I.; Fong, H. H. S.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 2002, 65, 532-536.
9. (e) Herz, W.; Bhat, S. V. J. Org. Chem. 1972, 37, 906-912.
10. (a) Hehner, S. P.; Heinrich, M.; Bork, P. M.; Vogt, M.; Ratter, F.; Lehmann, V.; Schulze-Osthoff, K.; Droge, W.; Schmitz, M. L. J. Biol. Chem. 1998, 273, 1288-1297.
11. (b) Lyss, G.; Knorre, A.; Schmidt, T. J.; Pahl, H. L.; Merfort, I. J. Biol Chem. 1998, 273, 33508-33516.
12. (c) Rüngeler, P.; Castro, V.; Mora, G.; Gören, N.; Vichnewski, W.; Pahl, H. L.; Merfort, I.; Schmidt, T. J. Bioorg. Med. Chem. 1999, 7, 2343-2352.
13. (d) García-Piñeres, A. J.; Castro, V.; Mora, G.; Schmidt, T. J.; Strunck, E.; Pahl, H. L.; Merfort, I. J. Biol. Chem. 2001, 276, 39713-39720.
14. For reviews on RCM, see: (a) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238.
15. (b) Armstrong, Susan K. J. Chem Soc., Perkin Trans. 1 1998, 371-388.
16. (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
17. (a) Nevalainen, M.; Koskinen, A. M. P. Angew. Chem., Int. Ed. 2001, 40, 4060-4062.
18. (b) Nevalainen, M.; Koskinen, A. M. P. J. Org. Chem 2002, 67, 1554-1560.
19. (c) Caggiano, L.; Castoldi, D.; Beumer, R.; Bayón, P.; Telser, J.; Gennari, C. Tetrahedron Lett. 2003, 44, 7913-7919.
20. (d) Beumer, R.; Bayón, P.; Bugada, P.; Ducki, S.; Mongelli, N.; Sirtori, F. R.; Telser, J.; Gennari, C. Tetrahedron 2003, 59, 8803-8820.
21. (e) Castoldi, D.; Caggiano, L.; Panigada, L.; Sharon, O.; Costa, A. M.; Gennari, C. Angew. Chem., Int. Ed. 2005, 44, 588-591.
22. (f) Castoldi, D.; Caggiano, L.; Bayón, P.; Costa, A. M.; Cappella, P.; Sharon, O.; Gennari, C. Tetrahedron 2005, 61, 2123-2139.
23. (g) Castoldi, D.; Caggiano, L.; Panigada, L.; Sharon, O.; Costa, A. M.; Gennari, C. Chem. Eur. J. 2006, 12, 51-62.
24. (a) Nacro, K.; Baltas, M.; Escudier, J.-M.; Gorrichon, L. Tetrahedron 1996, 52, 9047-9056.
25. (b) Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1991, 32, 5345-5348.
26. Evans, D. A.; Sjogren, E. B.; Bartroli, J.; Dow, R. L. Tetrahedron Lett. 1986, 27, 4957-4960.
27. For details, see Supporting Information.
28. For a recent review on selenolactonization, see: Jones, G. B.; Huber, R. S.; Chau, S. Tetrahedron 1993, 49, 369-380.
29. Scope and limitation as well as a mechanistic study of PhSeCl-mediated oxidative rearrangement of olefin will be reported elsewhere.
30. 4.
31. For example, see: Hanessian, S.; Giroux, S.; Larsson, A. Org. Lett. 2006, 8, 5481-5484 and references therein.
32. (a) Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160-17161.
33. (b) Larrosa, I.; Da Silva, M. I.; Gomez, P. M.; Hannen, P.; Ko, E.; Lenger, S. R.; Linke, S. R.; White, A. J. P.; Wilton, D.; Barrett, A. G. M. J. Am. Chem. Soc. 2006, 128, 14042-14043.