Amine-catalyzed epimerization of γ-hydroxybutenolides

Tetrahedron Letters

Volumn 48, Issue 44, 2007, Pages 7809-7812

  Miles, William H ^a   Duca, Daniela G ^a   Selfridge, Brandon R ^a   Palha De Sousa, Chiquita A ^a   Hamman, Kristin B ^a   Goodzeit, Elliot O ^a   Freedman, Jaryd T ^a  

^a LAFAYETTE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BUTENOLIDE; GAMMA HYDROXYBUTENOLIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHIRALITY; EPIMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 34848812555     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.017     Document Type: Article

References (58)

1. de Silva E.D., and Scheuer P.J. Tetrahedron Lett. 21 (1980) 1611-1614
2. Gunasekera S.P., McCarthy P.J., Kelly-Borges M., Lobkovsky E., and Clardy J. J. Am. Chem. Soc. 118 (1996) 8759-8760
3. Kernan M.R., Faulkner D.J., and Jacobs R.S. J. Org. Chem. 52 (1987) 3081-3083
4. De Rosa S., De Stefano S., and Zavodnik N. J. Org. Chem. 53 (1988) 5020-5023
5. De Rosa S., Crispino A., De Giulio A., Iodice C., Pronzato R., and Zavodnik N. J. Nat. Prod. 58 (1995) 1776-1780
6. Scio E., Ribeiro A., Alves T.M.A., Romanha A.J., de Souza Filho J.D., Cordell G.A., and Zani C.L. Phytochemistry 64 (2003) 1125-1131
7. Marcos I.S., Pedrero A.B., Sexmero M.J., Diez D., Basabe P., García N., Moro R.F., Broughton H.B., Mollinedo F., and Urones J.G. J. Org. Chem. 68 (2003) 7496-7504
8. Buchanan M.S., Edser A., King G., Whitmore J., and Quinn R.J. J. Nat. Prod. 64 (2001) 300-303
9. Kouno I., Hirai A., Fukushige A., Jiang Z., and Tanaka T. J. Nat. Prod. 64 (2001) 286-288
10. Montagnac A., Paǐs M., and Debitus C. J. Nat. Prod. 57 (1994) 186-190
11. De Rosa S., Crispino A., De Giulio A., Iodice C., and Tommonaro G. J. Nat. Prod. 60 (1997) 844-846
12. Randazzo A., Debitus C., Minale L., Pastor P.G., Alcaraz M.J., Payá M., and Gomez-Paloma L. J. Nat. Prod. 61 (1998) 571-575
13. Fontana A., Ciavatta M.L., and Cimino G. J. Org. Chem. 63 (1998) 2845-2849
14. Chang F., Hsieh T., Huang T., Chen C., Kuo R., Chang Y., Chiu H., and Wu Y. J. Nat. Prod. 65 (2002) 255-258
15. Sheu J., Wang G., Duh C., and Soong K. J. Nat. Prod. 66 (2003) 662-666
16. Patt W.C., Edmunds J.J., Repine J.T., Berryman K.A., Reisdorph B.R., Lee C., Plummer M.S., Shahripour A., Haleen S.J., Keiser J.A., Flynn M.A., Welch K.M., Reynolds E.E., Rubin R., Tobias B., Hallak H., and Doherty A.M. J. Med. Chem. 40 (1997) 1063-1074
17. Ellis J.E., Davis E.M., Dozeman G.J., Lenoir E.A., Belmont D.T., and Brower P.L. Org. Process Res. Dev. 5 (2001) 226-233
18. Lee G.C.M., Syage E.T., Harcourt D.A., Holmes J.M., and Garst M.E. J. Org. Chem. 56 (1991) 7007-7014
19. Lee G., De Vries G., Harcourt D., Holmes J., Amdahl L., Syage E., Wenzel M., Wheeler L., and Garst M. Drugs Future 15 (1990) 561-562
20. De Vries G.W., Lee G., Amdahl L., Wenzel M., Garst M., and Wheeler L.A. Agents Actions. 34 (1991) 70-72
21. Garst M.E., Tallman E.A., Bonfiglio J.N., Harcourt D., Ljungwe E.B., and Tran A. Tetrahedron Lett. 27 (1986) 4533-4536
22. Pommier A., Stepanenko V., Jarowicki K., and Kocienski P.J. J. Org. Chem. 68 (2003) 4008-4013
23. Soriente A., De Rosa M., Apicella A., Scettri A., and Sodano G. Tetrahedron: Asymmetry 10 (1999) 4481-4484
24. Coombs J., Lattmann E., and Hoffmann H.M.R. Synthesis (1998) 1367-1371
25. Katsumura S., Fujiwara S., and Isoe S. Tetrahedron Lett. 26 (1985) 5827-5830
26. Corey E.J., and Roberts B.E. J. Am. Chem. Soc. 119 (1997) 12425-12431
27. Boukouvalas J., Cheng Y., and Robichaud J. J. Org. Chem. 63 (1998) 228-229
28. Magnuson S.R., Sepp-Lorenzino L., Rosen N., and Danishefsky S.J. J. Am. Chem. Soc. 120 (1998) 1615-1616
29. Miyaoka H., Kajiwara Y., Hara Y., and Yamada Y. J. Org. Chem. 66 (2001) 1429-1435
30. Demeke D., and Forsyth C.J. Tetrahedron 58 (2002) 6531-6544
31. de la Torre M.C., García I., and Sierra M.A. J. Nat. Prod. 65 (2002) 661-668
32. Miyaoka H., Yamanishi M., Kajiwara Y., and Yamada Y. J. Org. Chem. 68 (2003) 3476-3479
33. Cheung A.K., Murelli R., and Snapper M.L. J. Org. Chem. 69 (2004) 5712-5719
34. Basabe P., Delgado S., Marcos I.S., Diez D., Diego A., De Román M., and Urones J.G. J. Org. Chem. 70 (2005) 9480-9485
35. Demeke D., and Forsyth C.J. Org. Lett. 5 (2003) 991-994
36. Murelli R.P., Cheung A.K., and Snapper M.L. J. Org. Chem. 72 (2007) 1545-1552
37. Gomez-Paloma L., Monti M.C., Terracciano S., Casapullo A., and Riccio R. Curr. Org. Chem. 9 (2005) 1419-1427
38. Valters R.E., and Flitsch W. In: Katritzky A.R. (Ed). Ring-Chain Tautomerism (1985), Plenum Press, New York
39. Seltzer S., and Stevens K.D. J. Org. Chem. 33 (1968) 2708-2711
40. McClelland R.A., and Sørensen P.E. Can. J. Chem. 64 (1986) 1196-1200
41. Bowden K., and Malik F.P. J. Chem. Soc., Perkin Trans. 2 (1993) 635-639
42. Bowden K., Mišić-Vuković M.M., and Ranson R.J. Collect. Czech. Chem. Commun. 64 (1999) 1601-1606
43. Fabian W.M.F., and Bowden K. Eur. J. Org. Chem. (2001) 303-309
44. Strizhov N.K., Poskonin V.V., Badovskaya L.A., and Kupina E.P. Russ. J. Org. Chem. 38 (2002) 251-255
45. Thuring J.W.J.F., Nefkens G.H.L., Wegman M.A., Klunder A.J.H., and Zwanenburg B. J. Org. Chem. 61 (1996) 6931-6935
46. Finkelstein J., Williams T., Toome V., and Traiman S. J. Org. Chem. 32 (1967) 3229-3230
47. Kagan J. J. Org. Chem. 32 (1967) 4060-4062
48. Santos L., Vargas A., Moreno M., Manzano B.R., Lluch J.M., and Douhal A. J. Phys. Chem. A 108 (2004) 9331-9341
49. 3 were at fast rate of exchange in the NMR.
50. Patil S.N., and Liu F. Org. Lett. 9 (2007) 195-198
51. Kobayashi M., Okamoto T., Hayashi K., Yokoyama N., Sasaki T., and Kitagawa I. Chem. Pharm. Bull. 42 (1994) 265-270 The authors suggest that manoalide isolated from a Palauan marine sponge of a Luffariella sp. was a single epimer of undefined stereochemistry but the manoalide isolated from the marine sponge Hyritios erecta was a mixture of epimers at the γ-hydroxybutenolide center
52. 3; the addition of dilute solutions of DABCO with rapid mixing circumvents this problem
53. Soriente A., Crispino A., De Rosa M., De Rosa S., Scettri A., Scognamiglio G., Villano R., and Sodano G. Eur. J. Org. Chem. (2000) 947-953
54. Bourguignon J.J., and Wermuth C.G. J. Org. Chem. 46 (1981) 4889-4894
55. 13C NMR spectrum with peaks that differed by less than 0.1 ppm (except for one set of carbons) from the spectrum reported in Ref. 33.
56. 3 or Hünig's base) to 4, Professor Liu (Ref. 33) provided good evidence for the generation of the fully formed open-chain carboxylate. When we add amines that are weaker bases (N-methylmorpholine or DABCO) in excess of what is needed for fast exchange of the epimers (10-25 mol %), there is not a significant change in the NMR spectra of the epimers of 1 or 4 at fast exchange, indicating the formation of only a small quantity of the open-chain carboxylate.
57. 13C NMR. The authors stated that 'since no unequivocal structure could be determined from these data', X-ray studies were undertaken. The authors also noted, however, that the proximity of the arms of dysidiolide may lead to hindered motions and hence the multiple peaks in the NMR. Since some of the NMR spectra of dysidiolide in subsequent synthetic studies have sharper peaks in the NMR, we suspect that impurities (or a lower concentration of HCl) in the NMR solvent are catalyzing the epimerization process.
58. Miles, W. H.; Duca, D. G.; Freedman, J. T.; Goodzeit, E. O.; Hamman, K. B.; Palha De Sousa, C. A.; Selfridge, B. R., Heterocyclic Commun., in press.