Studies toward the synthesis of spirolides: Assembly of the elaborated E-ring fragment

Organic Letters

Volumn 11, Issue 4, 2009, Pages 839-842

  Stivala, Craig E ^a   Zakarian, Armen ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; LITHIUM; SPIRO COMPOUND; SPIROLIDE C;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; LITHIUM; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 62749141553     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8027797     Document Type: Article

References (45)

1. (a) Hu, T.; Burton, I. W.; Cemella, A. D.; Curtis, J. M; Quilliam, M. A.; Walter, J. A.; Wright, J. L. C. J. Nat. Prod. 2001, 64, 308-312.
2. (b) Hu, T.; Curtis, J. M.; Oshima, Y.; Quilliam, M. A.; Walter, J. A.; Watson-Wright, W. M; Wright, J. L. C. J. Chem. Soc., Chem. Commun. 1995, 215, 9-2161.
3. (c) Falk, M.; Burton, I. W.; Hu, T.; Walter, J. A.; Wright, J. L. C. Tetrahedron 2001, 57, 8659-8665.
4. (a) Uemura, D.; Chuo, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S.; Chen, H. J. Am. Chem. Soc. 1995, 117, 1155-1156.
5. (b) Chou, T.; Kamo, O.; Uemura, D. Tetrahedron Lett. 1996, 37, 4023-4026.
6. (c) Chou, T.; Haino, T.; Kuramoto, M; Uemura, D. Tetrahedron Lett. 1996, 37, 4027-4030.
7. (a) Takada, N.; Umemura, N.; Suenaga, K.; Chou, T.; Nagatsu, A.; Haino, T.; Yamada, K.; Uemura, D. Tetrahedron Lett. 2001, 42, 3491-3494.
8. (b) Takada, N.; Umemura, N.; Suenaga, K.; Uemura, D. Tetrahedron Lett. 2001, 42, 3495-3497.
9. Seki, T.; Satake, M.; Mackenzie, L.; Kaspar, H.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 7093-7096.
10. Pinnatoxins A, B, and C: (a) McCauley, J. A.; Nagasawa, K.; Lander, P. A.; Mischke, S. G.; Semones, M. A.; Kishi, Y. J. Am. Chem. Soc. 1998, 120, 7647-7648.
11. (b) Stivala, C. E.; Zakarian, A. J. Am. Chem. Soc. 2008, 130, 3774-3776.
12. (c) Matsuuda, F.; Hao, J.; Reents, R.; Kishi, Y. Org. Lett. 2006, 8, 3327-3330.
13. (d) Nakamura, S.; Kikuchi, F.; Hashimoto, S. Angew. Chem., Int. Ed. 2008, 47, 7091-7094.
14. (e) Sakamoto, S.; Sakazaki, H.; Hagiwara, K.; Kamada, K.; Ishii, K.; Noda, T.; Inoue, M.; Hirama, M. Angew. Chem., Int. Ed. 2004, 43, 6505-6510. Pteriatoxins:
15. (f) Matsuura, F.; Peters, R.; Anada, M; Harried, S. S.; Hao, J.; Kishi, Y. J. Am. Chem. Soc. 2006, 128, 7463-7465.
16. (g) Hao, J.; Matsuura, F.; Kishi, Y.; Kita, M.; Uemura, D.; Asai, N.; Iwashita, T. J. Am. Chem. Soc. 2006, 128, 7742-7743.
17. Recent reports: (a) White, J. D.; Quaranta, L.; Wang, G. J. Org. Chem. 2007, 72, 1717-1728.
18. (b) Johannes, J. W.; Wenglowsky, S.; Kishi, Y. Org. Lett. 2005, 7, 3997-4000.
19. (c) Kong, K.; Moussa, Z.; Romo, D. Org. Lett. 2005, 7, 5127-5130.
20. (a) Meilert, K.; Brimble, M. A. Org. Lett. 2005, 7, 3497-3500.
21. (b) Furkert, D. P.; Brimble, M. A. Org. Lett. 2002, 4, 3655-3658.
22. (c) Meilert, K.; Brimble, M. A. Org. Biomol. Chem. 2006, 4, 2184-2192.
23. (d) Brimble, M. A.; Caprio, V.; Furkert, D. P. Tetrahedron 2001, 57, 4023-4034.
24. (e) Brimble, M. A.; Fares, F. A.; Turner, P. Aust. J. Chem. 2000, 53, 845-851.
25. Ishihara, J.; Ishizaka, T.; Suzuki, T.; Hatakeyama, S. Tetrahedron Lett. 2004, 45, 7855-7858.
26. (a) Brimble, M. A.; Trzoss, M. Tetrahedron 2004, 60, 5613-5622.
27. (b) Trzoss, M.; Brimble, M. A. Synlett., 2003, 2042-2046.
28. (a) Qin, Y.-c.; Stivala, C. E.; Zakarian, A. Angew. Chem., Int. Ed. 2007, 46, 7466-7469.
29. (a) O'Brien, P.; Poumellec, P. Tetrahedron Lett. 1996, 37, 5619-5622.
30. (b) Curthbertson, E.; O'Brien, P.; Towers, T. D. Synthesis 2001, 5, 693-695.
31. (a) Saravanan, P.; Singh, V. K. Tetrahedron Lett. 1998, 39, 167-170.
32. (b) Saravanan, P.; Bisai, A.; Baktharaman, S.; Chandrasekhar, M.; Singh, V. K. Tetrahedron 1998, 58, 4693-4706.
33. Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180-5182.
34. Prakash, C.; Saleh, S.; Blair, I. A. Tetrahedron Lett. 1989, 30, 19-22.
35. Stivala, C. E.; Zakarian, A. Tetrahedron Lett. 2007, 48, 6845-6848.
36. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
37. (a) Sullivan, D. F.; Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1977, 42, 2038-2039.
38. (b) Seebach, D.; Amstutz, R.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Am. Chem. Soc. 1985, 107, 5403-5409.
39. Varying concentration, number of equivalents of LDA, and reaction time led to decomposition and/or incomplete reactions.
40. For a recent review on (trimethylsilyl) diazomethane, see: Kühnel, E.; Laffan, D. D.; Lloyd-Jones, G. C.; del Campo, T. M.; Shepperson, I. R.; Slaughter, J. L. Angew. Chem., Int. Ed. 2007, 46, 7075-7078.
41. Schwartz, C.; Raible, J.; Mott, K.; Dussault, P. H. Org. Lett. 2006, 8, 3199-3201.
42. Corey, E. J.; Danheiser, R. L.; Chandrasekaran, S.; Siret, R.; Keck, G. E.; Gras, J.-L. J. Am. Chem. Soc. 1978, 100, 8031-8034.
43. Larock, R. C.; Yang, H.; Weinreb, S. M.; Herr, R. J. J. Org. Chem. 1994, 59, 4172-4178.
44. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
45. (b) Boeckman, R. K.; Shao, P.; Mullins, J. J. Org. Synth. 2000, 77, 141.