A novel synthesis of γ-lactones by tandem epoxide opening-cyclization reaction mediated by samarium(II) diiodide

Tetrahedron Letters

Volumn 49, Issue 10, 2008, Pages 1616-1618

  Park, Heui Sul ^a   Kwon, Doo Won ^a   Lee, Kieseung ^b   Kim, Yong Hae ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Woosuk University   (South Korea)

Author keywords

Butyrolactone; Lactone; Samarium diiodide; Tandem reaction

Indexed keywords

BROMOACETIC ACID; EPOXIDE; ESTER; GAMMA LACTONE DERIVATIVE; SAMARIUM DIIODIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 38949177363     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.027     Document Type: Article

References (37)

1. Koch S.S.C., and Chamberlin A.R. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry Vol. 16 (1995), Elsevier, Amsterdam 687-725
2. Rao Y.S. Chem. Rev. 76 (1976) 625
3. Hoffmann H.M.R., and Rabe J. Angew. Chem., Int. Ed. Engl. 24 (1985) 94
4. Mulzer J., Salimi N., and Hartl H. Tetrahedron: Asymmetry 4 (1993) 457
5. Schmitz W.D., Messerschmidt N.B., and Romo D. J. Org. Chem. 63 (1998) 2058
6. Maier M.S., Marimon D.I.G., Stortz C.A., and Adler M.J. J. Nat. Prod. 62 (1999) 1565
7. Harchen C., and Bruckner R. Angew. Chem., Int. Ed. 36 (1997) 2750
8. Drioli S., Felluga F., Forzato C., Nitti P., Pitacco G., and Valentin E. J. Org. Chem. 63 (1998) 2385
9. de March P., Figueredo M., Font J., and Raya J. Org. Lett. 2 (2000) 163
10. He M., Lei A., and Zhang X. Tetrahedron Lett. 46 (2005) 1823
11. Delhaye L., Merschaert A., Diker K., and Houpis I.N. Synthesis (2006) 1437
12. Gutierrez J.L.G., Jimenez-Cruz F., and Espinosa N.R. Tetrahedron Lett. 46 (2005) 803
13. Burstein C., Tschan S., Xie X., and Glorius F. Synthesis (2006) 2418
14. Tiecco M., Testaferri L., Temperini A., Terlizzi R., Bagnoli L., Marini F., and Santi C. Synlett (2006) 587
15. Vitale M., Prestat G., Lopes D., Madec D., and Poli G. Synlett (2006) 2231
16. Cho C.S., and Shim H.S. Tetrahedron Lett. 47 (2006) 3835
17. Dias L.C., de Castro I.B.D., Steil L.J., and Augusto T. Tetrahedron Lett. 47 (2006) 213 Other important references cited therein
18. Namy J.-L., Girard P., and Kagan H.B. Nouv. J. Chim. 1 (1977) 5
19. Girard P., Namy J.L., and Kagan H.B. J. Am. Chem. Soc. 102 (1980) 2693
20. Kwon D.W., Cho M.S., and Kim Y.H. Synlett (2003) 959
21. Chung S.H., Cho M.S., Choi J.Y., Kwon D.W., and Kim Y.H. Synlett (2001) 1266
22. Jung D.Y., and Kim Y.H. Synlett (2005) 3019
23. Epoxy esters 2a-e were prepared in two steps via allylation of malonates followed by epoxidation with m-CPBA.
24. 4: 297.9702; found: 297.9713.
25. Shiu L.-H., Li Y.-L., Lao C.-Y., Chen W.-C., Yu C.-H., and Liu R.-S. J. Org. Chem. 64 (1999) 7552
26. Velazquez F., and Olivo H.F. Org. Lett. 2 (2000) 1931
27. Bergner E.J., and Helmchen G. J. Org. Chem. 65 (2000) 5072
28. Zanoni G., Porta A., Meriggi A., Franzini M., and Vidari G. J. Org. Chem. 67 (2002) 6064
29. Ginn J., and Padwa A. Org. Lett. 4 (2002) 1515
30. Trost B.M., Balkove J.M., and Mao M.K.-T. J. Am. Chem. Soc. 105 (1983) 6755
31. Peterson E.M., Xu K., Holland K.D., Mckeon A.C., Rothman S.M., Ferrendelli J.A., and Covey D.F. J. Med. Chem. 37 (1994) 275
32. Silva L.F.J. Synthesis (2001) 671
33. Vyvyan J.R., Rubens C.A., and Halfen J.A. Tetrahedron Lett. 43 (2002) 221
34. Kupchan S.M., Fessler D.C., Eakin M.A., and Giacobbe T.J. Science 168 (1970) 376
35. Iio H., Isobe M., Kawai T., and Goto T. J. Am. Chem. Soc. 101 (1979) 6067
36. Bartel S., and Bohlmann F. Tetrahedron Lett. 30 (1989) 685
37. Gonzalez A.G., Hernandez S., Margarita P., Juan I., Leon F., Reyes E., Alvarez-Mon M., Pivel J.P., Quintana J., Estevez F., and Bermejo J. J. Med. Chem. 45 (2002) 2358