Total synthesis of (-)-anisatin

Organic Letters

Volumn 14, Issue 6, 2012, Pages 1632-1635

  Ogura, Akihiro ^a   Yamada, Kohei ^a   Yokoshima, Satoshi ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANISATIN; LACTONE; QUINONE DERIVATIVE; RHODIUM; SESQUITERPENE; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; ILLICIUM; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; ILLICIUM; LACTONES; OXIDATION-REDUCTION; QUINONES; RHODIUM; SESQUITERPENES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84858684413     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300390k     Document Type: Article

References (43)

1. Lane, J. F.; Koch, W. T.; Leeds, N. S.; Gorin, G. J. Am. Chem. Soc. 1952, 74, 3211
2. Yamada, K.; Takeda, S.; Nakamura, S.; Hirata, Y. Tetrahedron Lett. 1965, 6, 4797
3. Yamada, K.; Takada, S.; Nakamura, S.; Hirata, Y. Tetrahedron 1968, 24, 199
4. Shinozaki, H.; Ishida, M.; Kudo, Y. Brain Res. 1981, 222, 401
5. Kudo, Y.; Oka, J.; Yamada, K. Neurosci. Lett. 1981, 25, 83
6. Matsumoto, K.; Fukuda, H. Neurosci. Lett. 1982, 32, 175
7. Matsumoto, K.; Fukuda, H. Brain Res. 1983, 270, 103
8. Kakemoto, E.; Okuyama, E.; Nagata, K.; Ozoe, Y. Biochem. Pharmacol. 1999, 58, 617
9. Ikeda, T.; Ozoe, Y.; Okuyama, E.; Nagata, K.; Honda, H.; Shono, T.; Narahashi, T. Br. J. Pharmacol. 1999, 127, 1567
10. Kuriyama, T.; Schmidt, T. J.; Okuyama, E.; Ozoe, Y. Bioorg. Med. Chem. 2002, 10, 1873
11. Schmidt, T. J.; Gurrath, M.; Ozoe, Y. Bioorg. Med. Chem. 2004, 12, 4159
12. Lindner, D. L.; Doherty, J. B.; Shoham, G.; Woodward, R. B. Tetrahedron Lett. 1982, 23, 5111
13. Kato, M.; Kitahara, H.; Yoshikoshi, A. Chem. Lett. 1985, 14, 1785
14. Kende, A. S.; Chen, J. J. Am. Chem. Soc. 1985, 107, 7184
15. Niwa, H.; Mori, T.; Hasegawa, T.; Yamada, K. J. Org. Chem. 1986, 51, 1015
16. Charonnat, J. A.; Nishimura, N.; Travers, B. W.; Waas, J. R. Synlett 1996, 1162
17. Loh, T.-P.; Hu, Q.-Y. Org. Lett. 2001, 3, 279
18. Urabe, D.; Inoue, M. Tetrahedron 2009, 65, 6271
19. Niwa, H.; Nisiwaki, M.; Tsukada, I.; Ishigaki, T.; Ito, S.; Wakamatsu, K.; Mori, T.; Ikagawa, M.; Yamada, K. J. Am. Chem. Soc. 1990, 112, 9001
20. Liao, C.-C.; Peddinti, R. K. Acc. Chem. Res. 2002, 35, 856
21. Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383
22. Pouysegu, L.; Deffieux, D.; Quideau, S. Tetrahedron 2010, 66, 2235
23. Roche, S. P.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2011, 50, 4068
24. Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229
25. Navarro, C.; Moreno, A.; Csákÿ, A. G. J. Org. Chem. 2009, 74, 466
26. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169
27. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829
28. Caturla Javaloyes, J. F.; Vidal Gispert, L.; Lumeras Amador, W. WO2008/017461, 2008.
29. Moradei, O. M.; Paquette, L. A. Org. Synth. 2003, 80, 66
30. Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496
31. Ikeya, Y.; Taguchi, H.; Yoshioka, I. Chem. Pharm. Bull. 1981, 29, 2893
32. Seitz, D. E.; Carroll, J. J.; Cartaya, M. C. P.; Lee, S.; Zapata, A. Synth. Commun. 1983, 13, 129
33. Depuy, C. H.; King, R. W. Chem. Rev. 1960, 60, 431
34. Nace, H. R. Org. React. 1962, 12, 57
35. Nakai, T.; Mikami, K. Org. React. 1994, 46, 105
36. Atkins, G. M.; Burgess, E. M. J. Am. Chem. Soc. 1968, 90, 4744
37. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136
38. Nicolaou, K. C.; Hepworth, D.; King, N. P.; Finlay, M. R. V.; Scarpelli, R.; Pereira, M. M. A.; Bollbuck, B.; Bigot, A.; Werschkun, B.; Winssinger, N. Chem. - Eur. J. 2000, 6, 2783
39. For an example of the cleavage of an epoxide by a primary amide to provide a lactone, see: Wuts, P. G. M.; Ritter, A. R.; Pruitt, L. E. J. Org. Chem. 1992, 57, 6696
40. Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175
41. Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825
42. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091
43. Shiina, I.; Ibuka, R.; Kubota, M. Chem. Lett. 2002, 31, 286