Synthesis of β,β-disubstituted-α-methylene-γ-butyrolactones via the regioselective oxidation of exo-methylenetetrahydrofurans

Tetrahedron Letters

Volumn 48, Issue 2, 2007, Pages 289-292

  Gowrisankar, Saravanan ^a   Kim, Seong Jin ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Methylene butyrolactones; Baylis Hillman adducts; Jones oxidation; PCC Ac2O; Regioselective oxidation

Indexed keywords

LACTONE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; JONES OXIDATION; OXIDATION; SUBSTITUTION REACTION;

EID: 33845186599     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.031     Document Type: Article

References (38)

1. For the synthesis and biological activities of α-methylene-γ-butyrolactones, see:. Yu S.H., Ferguson M.J., McDonald R., and Hall D.G. J. Am. Chem. Soc. 127 (2005) 12808
2. Kennedy J.W.J., and Hall D.G. J. Am. Chem. Soc. 124 (2002) 11586
3. Kennedy J.W.J., and Hall D.G. J. Org. Chem. 69 (2004) 4412
4. Sidduri A.-R., and Knochel P. J. Am. Chem. Soc. 114 (1992) 7579
5. Sidduri A.-R., Rozema M.J., and Knochel P. J. Org. Chem. 58 (1993) 2694
6. Peng H., Kim D.-I., Sarkaria J.N., Cho Y.-S., Abraham R.T., and Zalkow L.H. Bioorg. Med. Chem. 10 (2002) 167
7. Nozaki K., Oshima K., and Utimoto K. Bull. Chem. Soc. Jpn. 60 (1987) 3465
8. Kennedy J.W.J., and Hall D.G. J. Am. Chem. Soc. 124 (2002) 898
9. Kennedy J.W.J., and Hall D.G. J. Am. Chem. Soc. 124 (2002) 11586
10. Koreeda M., Ricca D.J., and Luengo J.I. J. Org. Chem. 53 (1988) 5886
11. For the synthesis of natural products containing β-carboxy-α-methylene-γ-butyrolactone skeleton and related structures, see:. Mandal P.K., Maiti G., and Roy S.C. J. Org. Chem. 63 (1998) 2829
12. Sarkar S., and Ghosh S. Tetrahedron Lett. 37 (1996) 4809
13. Ghatak A., Sarkar S., and Ghosh S. Tetrahedron 53 (1997) 17335
14. Loh T.-P., and Lye P.-L. Tetrahedron Lett. 42 (2001) 3511
15. Saicic R.N., and Zard S.Z. Chem. Commun. (1996) 1631
16. Maiti G., and Roy S.C. J. Chem. Soc., Perkin Trans. 1 (1996) 403
17. Hon Y.-S., Hsieh C.-H., and Liu Y.-W. Tetrahedron 61 (2005) 2713
18. Bella M., Margarita R., Orlando C., Orsini M., Parlanti L., and Piancatelli G. Tetrahedron Lett. 41 (2000) 561
19. Drioli S., Felluga F., Forzato C., Nitti P., Pitacco G., and Valentin E. J. Org. Chem. 63 (1998) 2385
20. Pohmakotr M., Harnying W., Tuchinda P., and Reutrakul V. Helv. Chim. Acta 85 (2002) 3792
21. Biel M., Kretsovali A., Karatzali E., Papamatheakis J., and Giannis A. Angew. Chem., Int. Ed. 43 (2004) 3974
22. Forbes J.E., Saicic R.N., and Zard S.Z. Tetrahedron 55 (1999) 3791
23. Mawson S.D., and Weavers R.T. Tetrahedron 51 (1995) 11257
24. For the oxidation of tetrahydrofurans into α-methylene-γ-butyrolactones and related reactions, see:. Charruault L., Michelet V., and Genet J.-P. Tetrahedron Lett. 43 (2002) 4757
25. Srikrishna A. J. Chem. Soc., Chem. Commun. (1987) 587
26. Liu Z.-Y., Zhou X.-R., and Wu Z.-M. J. Chem. Soc., Chem. Commun. (1987) 1868
27. Blanchot-Courtois V., Fetizon M., and Hanna I. Tetrahedron Lett. 33 (1992) 5061
28. Bonadies F., Fabio R.D., and Bonini C. J. Org. Chem. 49 (1984) 1647
29. For the synthesis of lactones starting from the Baylis-Hillman adducts, see:. Paquette L.A., and Mendez-Andino J. Tetrahedron Lett. 40 (1999) 4301
30. Kabalka G., and Venkataiah B. Tetrahedron Lett. 46 (2005) 7325
31. Breitenstein K., Llebaria A., and Delgado A. Tetrahedron Lett. 45 (2004) 1511
32. Lee K.Y., Park D.Y., and Kim J.N. Bull. Korean Chem. Soc. 27 (2006) 1489
33. For the synthesis of starting materials 1a-d and the synthetic applications, see:. Gowrisankar S., Lee K.Y., and Kim J.N. Tetrahedron Lett. 46 (2005) 4859 and references cited therein
34. 2O system in oxidations, see:. Kim J.N., and Ryu E.K. Tetrahedron Lett. 33 (1992) 3141
35. Classon B., and Samuelsson B. Acta Chem. Scand. B 39 (1985) 501
36. 3, 300 MHz) δ 1.20 (t,J = 7.2 Hz, 3H), 2.28 (d, J = 2.1 Hz, 3H), 3.80 (s, 3H), 4.11-4.30 (m, 2H), 5.97-6.00 (m, 1H), 6.87 (d, J = 9.0 Hz, 2H), 7.17 (d, J = 9.0 Hz, 2H).
37. For the synthesis of 1e and 1f and the synthetic applications, see:. Gowrisankar S., Park D.Y., and Kim J.N. Bull. Korean Chem. Soc. 26 (2005) 1826 and references cited therein
38. For the synthesis of 1g and the synthetic applications, see:. Gowrisankar S., Lee K.Y., and Kim J.N. Tetrahedron 62 (2006) 4052 and references cited therein