Carbonylative lactonization via carbonyl oxygen attack: A short and selective total synthesis of uncinine and its analogues

Tetrahedron Letters

Volumn 46, Issue 47, 2005, Pages 8137-8140

  Fáková, Helena ^a   Pour, Milan ^a   Kuneš, Jiří ^a   Šenel, Petr ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

Author keywords

Alkaloids; Butenolides; Carbonylative lactonization; Cytotoxicity; Pd catalysis

Indexed keywords

ALCOHOL DERIVATIVE; ALKALOID DERIVATIVE; AMINOBUTYRIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CYTOTOXIC AGENT; KETONE DERIVATIVE; OXYGEN; SUCCINIMIDE DERIVATIVE; UNCININE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; DRUG SYNTHESIS; SUBSTITUTION REACTION;

EID: 27144518434     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.128     Document Type: Article

References (44)

1. T.-J. Hsieh, F.-R. Chang, Y.-C. Chia, C.-Y. Chen, H.-C. Lin, H.-F. Chiu, and Y.-C. Wu J. Nat. Prod. 64 2001 1157 1161
2. For a review on piracetam-derived nootropics, see: F. Gualtieri, D. Manetti, M.N. Romanelli, and C. Ghelardini Curr. Pharm. Design 8 2002 125 138
3. N. Didry, L. Dubreuil, and M. Pinkas Phytotherapy Res. 7 1993 21 24
4. M.L. Martin, L.S. Roman, and A. Dominguez Planta Med. 56 1990 66 69
5. S.C. Miao, and R.J. Andersen J. Org. Chem. 56 1991 6275 6280
6. D. Kuhnt, T. Anke, H. Besl, M. Bross, R. Herrmann, U. Mocek, B. Steffan, and W. Steglich J. Antibiot. 43 1990 1413 1420
7. For reviews on butenolide synthesis, see: D.W. Knight Contemp. Org. Synth. 1 1994 287 315
8. N.B. Carter, A.E. Nadany, and J.B. Sweeney J. Chem. Soc., Perkin Trans. 1 2002 2324 2342
9. For an excellent review on γ-alkylidene butenolide synthesis, see: E. Negishi, and M. Kotora Tetrahedron 53 1997 6707 6738
10. R. Brückner Curr. Org. Chem. 5 2001 679 718
11. For recent examples, see: C. Piper, and N. Risch Arkivoc 2003 86 92
12. S.-C. Bang, Y. Kim, M.-Y. Yun, and B.-Z. Ahn Arch. Pharm. Res. 27 2004 485 494
13. For recent examples, see: M. Pohmakotr, P. Tuchinda, P. Premkaisorn, and V. Reutrakul Tetrahedron 54 1998 11297 11304
14. J. Boukouvalas, N. Lachance, M. Ouellet, and M. Trudeau Tetrahedron Lett. 39 1998 7665 7668
15. F. Bellina, Ch Anselmi, S. Viel, L. Mannina, and R. Rossi Tetrahedron 57 2001 9997 10007
16. F. Bellina, Ch. Anselmi, and R. Rossi Tetrahedron Lett. 43 2002 2023 2027
17. F. Bellina, Ch. Anselmi, F. Martina, and R. Rossi Eur. J. Org. Chem. 2003 2290 2302
18. For a recent example, see: X.-C. Li, D. Ferreira, M.R. Jacob, Q. Zhang, S.I. Khan, H.N. ElSohly, D.G. Nagle, T.J. Smillie, I.A. Khan, L.A. Walker, and A.M. Clark J. Am. Chem. Soc. 126 2004 6872 6873
19. A. Sorg, K. Siegel, and R. Brückner Synlett 2004 321 325 (a recent procedure)
20. A. Sorg, and R. Brückner Angew. Chem., Int. Ed. 43 2004 4523 4526 (total synthesis)
21. C. Copéret, T. Sugihara, G. Wu, I. Shimoyama, and E. Negishi J. Am. Chem. Soc. 117 1995 3422 3431
22. For the development of methodology, see: M. Kotora, and E. Negishi Synthesis 1997 121 128
23. R. Rossi, F. Bellina, and L. Mannina Tetrahedron Lett. 39 1998 3017 3020
24. S. Rousset, M. Abarbri, J. Thibonnet, A. Duchêne, and J.-L. Parrain Org. Lett. 1 1999 701 703
25. R. Rossi, F. Bellina, M. Biagetti, A. Catanese, and L. Mannina Tetrahedron Lett. 41 2000 5281 5286
26. E. Rousset, J. Thibonnet, M. Abarbri, A. Duchêne, and J.-L. Parrain Synlett 2000 260 262
27. L. Anastasia, C. Xu, and E. Negishi Tetrahedron Lett. 43 2002 5673 5676
28. S. Rousset, M. Abarbri, J. Thibonnet, J.-L. Parrain, and A. Duchêne Tetrahedron Lett. 44 2003 7633 7636
29. R. Brückner Chem. Commun. 2001 141 152
30. For recent total syntheses, see: F. Liu, and E. Negishi J. Org. Chem. 62 1997 8591 8594
31. R. Rossi, F. Bellina, M. Biagetti, and L. Mannina Tetrahedron Lett. 39 1998 7799 7802
32. C. Xu, and E. Negishi Tetrahedron Lett. 40 1999 431 434
33. E. Negishi, A. Alimardanov, and C. Xu Org. Lett. 2 2000 65 67
34. R. Rossi, F. Bellina, A. Catanese, L. Mannina, and D. Valensin Tetrahedron 56 2000 479 487
35. V. Fiandanese, D. Bottalico, G. Marchese, and A. Punzi Tetrahedron 60 2004 11421 11425
36. N. Furuichi, H. Hara, T. Osaki, M. Nakano, H. Mori, and S. Katsumura J. Org. Chem. 69 2004 7949 7959
37. S.E. Denmark, and T.K. Jones J. Org. Chem. 47 1982 4595 4597
38. R. Schiller, M. Pour, H. Fáková, J. Kuneš, and I. Císařová J. Org. Chem. 69 2004 6761 6765
39. Only slight decomposition was observed when compound 3 was stored at -18°C for 10 months, while storing at 0°C led to complete decomposition in less than 3 months.
40. The best yields achieved in the deprotection step were around 70%, confirming an obvious assumption that γ-alkylidene butenolides are also acid sensitive.
41. E.J. Corey, C.U. Kim, and M. Takeda Tetrahedron Lett. 13 1972 4339 4342
42. A similar approach (treatment of carbonyl compounds with amino esters followed by in situ reduction and spontaneous cyclization) has been used by Abdel-Magid and co-workers, see A.F. Abdel-Magid, B.D. Harris, and C.A. Maryanoff Synlett 1994 81 83
43. 2 giving rise to carbamates, see e.g.
44. K. Vávrová, A. Hrabálek, P. Doležal, T. Holas, and J. Klimentová J. Contr. Release 104 2005 41 49