Palladium-catalyzed oxidative cyclization in alkaloid synthesis: Total syntheses of (±)-cis- and trans-195A

Tetrahedron Letters

Volumn 51, Issue 35, 2010, Pages 4620-4622

  Saeki, Megumi ^a   Toyota, Masahiro ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

195A; ALKALOID DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; BECKMANN REARRANGEMENT; CATALYSIS; CIS TRANS ISOMERISM; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 77955652926     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.114     Document Type: Article

References (28)

1. A. Hibi, and M. Toyota Tetrahedron Lett. 50 2009 4888 4891
2. Original paper: M. Toyota, T. Wada, K. Fukumoto, and M. Ihara J. Am. Chem. Soc. 120 1998 4916 4925
3. Review: M. Toyota, and M. Ihara Synlett 2002 1211 1222
4. Applications: M. Toyota, A. Ilangovan, R. Okamoto, M. Masaki, M. Arakawa, and M. Ihara Org. Lett. 4 2002 4293 4296
5. M. Toyota, M. Rudyanto, and M. Ihara J. Org. Chem. 67 2002 3374 3386
6. Aphidicolin synthesis: M. Toyota, M. Sasaki, and M. Ihara Org. Lett. 8 2003 1193 1195
7. Serofendic acids synthesis: M. Toyota, T. Asano, and M. Ihara Org. Lett. 7 2005 3929 3932
8. Isolation: J.W. Daly, T. Tokuyama, G. Habermehl, I.L. Karle, and B. Witkop Liebigs Ann. Chem. 729 1969 198 204
9. Physiological property: J.W. Daly, Y. Nishizawa, W.L. Padgett, T. Tokuyama, P.J. McCloskey, L. Waykole, A.G. Schultz, and R.S. Aronstam Neurochem. Res. 16 1991 1207 1212
10. Recent total syntheses: A. Padwa, T.M. Heidelbaugh, and J.T. Kuethe J. Org. Chem. 65 2000 2368 2378
11. W. Oppolzer, E. Flaskamp, and L. Bicher Helv. Chim. Acta 84 2001 141 145
12. M. Akashi, Y. Sato, and M. Mori J. Org. Chem. 66 2001 7873 7874
13. E.W. Dijk, L. Panella, P. Pinho, R. Naasz, A. Meetsma, A.J. Minnaard, and B.L. Feringa Tetrahedron 60 2004 9687 9693
14. N. Girard, J.-P. Hurvois, C. Moinet, and L. Toupet Eur. J. Org. Chem. 2005 2269 2280
15. M. Amat, R. Griera, R. Fabregat, E. Molins, and J. Bosch Angew. Chem., Int. Ed. 47 2008 3348 3351
16. S. Lauson, F. Tremblay, D. Gagnon, C. Godbout, C. Chabot, C. Mercier-Shanks, S. Perreault, H. DeSeve, and C. Spino J. Org. Chem. 73 2008 6239 6250
17. Our syntheses: M. Toyota, T. Asoh, M. Matsuura, and K. Fukumoto J. Org. Chem. 61 1996 8687 8691
18. M. Toyota, T. Asoh, and K. Fukumoto Tetrahedron Lett. 37 1996 4401 4404
19. W. Oppolzer, C. Fehr, and J. Warneke Helv. Chim. Acta 60 1977 48 58
20. Y. Aubin, G. Audran, and H. Monti Tetrahedron Lett. 47 2006 3669 3671
21. +), 210.1256, found 210.1261.
22. Cieplak, A. S. Chem. Rev. 1999, 99, 1265-1336.
23. Similar result was observed by Yamamoto and co-workers: Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831-2843.
24. Additionally, stereoelectronic effects predict the stereochemical preferences in 14 and 17, respectively. (a) Stevens, R. V. Acc. Chem. Res. 1984, 17, 289-296.
25. (b) Deslongchamps, P. Stereoelectonic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983; pp 211-221.
26. H.M. Garraffo, L.D. Simon, J.W. Daly, T.F. Spande, and T.H. Jones Tetrahedron 50 1994 1329-11338
27. T.F. Spande, P. Jain, H.M. Garraffo, L.K. Pannell, H.J.C. Yeh, J.W. Daly, S. Fukumoto, T. Tokuyama, Torres, R.R. Snelling, and T.H. Jones J. Nat. Prod. 62 1999 5 21
28. Total synthesis of (+)-trans-195A: N. Holub, J. Neidhöfer, and S. Blechert Org. Lett. 7 2005 1227 1229