A practical one-pot radical-ionic sequence for the preparation of epoxides: Application to the synthesis of unnatural polyhydroxylated alkaloids

Tetrahedron Letters

Volumn 52, Issue 51, 2011, Pages 6899-6902

  Peralta Hernández, Eduardo ^a   Cortezano Arellano, Omar ^a   Cordero Vargas, Alejandro ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Atom transfer reaction; Epoxides; Free radical; Polyhydroxylated alkaloids

Indexed keywords

ALCOHOL; ALKALOID DERIVATIVE; AZULENE; CASTANOSPERMINE; EPOXIDE; RADICAL;

ARTICLE; EPOXIDATION; ONE POT SYNTHESIS; SYNTHESIS;

EID: 81255201336     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.042     Document Type: Article

References (24)

1. L.D. Hohenschutz, E.A. Bell, P.J. Jewess, D.P. Leworthy, R.J. Pryce, E. Arnold, and J. Clardy Phytochemistry 20 1981 811
2. R.J. Nash, L.E. Fellows, J.V. Dring, C.H. Stirton, D. Carter, M.P. Hegarty, and E.A. Bell Phytochemistry 27 1988 1403
3. F.P. Guennguerich, S.J. DiMari, and H.P. Broquist J. Am. Chem. Soc. 95 1973 2055
4. For a review on the synthesis of swainsonine and lentiginosine, see: A.E. Nemr Tetrahedron 56 2000 8579
5. For a recent synthesis, see: S. Chooprayoon, C. Kuhakarn, P. Tuchinda, V. Reutrakul, and M. Pohmaktor Org. Biomol. Chem. 9 2011 531
6. I. Pastuszak, R.J. Molyneux, L.F. James, and A.D. Elbein Biochemistry 29 1990 1886
7. J.P. Michael Nat. Prod. Rep. 18 2001 520
8. For reviews on polyhydroxylated alkaloids, see: P. Sears, and C.-H. Wong Angew. Chem., Int. Ed. 38 1999 2300
9. Y. Chen, and P. Vogel J. Org. Chem. 59 1994 2487
10. J. Michael Nat. Prod. Rep. 21 2004 625
11. K. Burguess, and I. Henderson Tetrahedron 48 1992 4045
12. S.D. Markad, N.S. Karanjule, T. Sharma, S.G. Sabharwal, and D.D. Dhavale Org. Biomol. Chem. 4 2006 3675
13. K.S.A. Kumar, V.D. Chaudhari, and D.D. Dhavale Org. Biomol. Chem. 6 2008 703
14. N. Wang, L.-H. Zhang, and X.-S. Ye Org. Biomol. Chem. 8 2010 2639
15. S.D. Markad, N.S. Karanjule, T. Sharma, S.G. Sabharwal, V.G. Puranik, and D.D. Dhavale Org. Biomol. Chem. 4 2006 2549
16. J. Byers P. Renaud, M.P. Sibi, Radicals in Organic Synthesis 2001 Wiley-VCH Weinheim 72 89
17. Atom transfer radical reactions can also be catalyzed by Cu(I). For a review, see: W.T. Eckenhoff, and T. Pintauer Cat. Rev. 52 2010 1
18. H. Yorimitsu, T. Nakamura, H. Shinokubo, K. Oshima, K. Omoto, and H. Fujimoto J. Am. Chem. Soc. 122 2000 11041
19. K. Nozaki, K. Oshima, and K. Utimoto Bull. Chem. Soc. Jpn. 64 1991 403
20. Y. Horiuchi, M. Taniguchi, K. Oshima, and K. Utimoto Tetrahedron Lett. 36 1995 5353
21. S. Chandrasekhar, C. Narsihmulu, N. Reddy, and S. Reddy Tetrahedron Lett. 44 2003 2583
22. B. Giese Angew. Chem., Int. Ed. 22 1983 753
23. J.M. Tedder, and J.C. Walton Acc. Chem. Res. 9 1976 183
24. S. Caddick, D.B. Judd, A.K.K. Lewis, M.T. Reich, and R.V. Williams Tetrahedron 59 2003 5417