Polycyclic phosphonic acid derivatives obtained by a [4+2] cycloaddition strategy using phosphonodienes

Tetrahedron

Volumn 69, Issue 3, 2013, Pages 1138-1147

  Villemin, Elise ^a   Robeyns, Koen ^a   Robiette, Raphael ^a   Herent, Marie France ^a   Marchand Brynaert, Jacqueline ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

1 Phosphonodienes; Benzyl deprotection; Diels Alder reaction; Horner Wadsworth Emmons reaction; Phosphonic acid

Indexed keywords

1 PHOSPHONO 3(4 DI)SUBSTITUTED 1,3 BUTADIENE DERIVATIVE; ALKADIENE; DIBENZYL 1 PHOSPHONO 1,3 BUTADIENE; DIETHYL 1 PHOSPHONO 1,3 BUTADIENE; PHOSPHONIC ACID DERIVATIVE; POLYCYCLIC PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; HORNER WADSWORTH EMMONS REACTION; PRIORITY JOURNAL;

ALNUS;

EID: 84871624519     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.11.059     Document Type: Article

References (49)

1. K.N. Anisimov, and N.E. Kolobova Bull. Acad. Sci. USSR, Div. Chem. Sci. 1956 943 946
2. B.V. Ryabov, B.I. Ionin, and A.A. Petrov J. Gen. Chem. USSR 58 1988 969 983
3. W. Welter, A. Hartmann, and M. Regitz Chem. Ber. 111 1978 3068 3085
4. C. Wang, Y. Pan, and D. Yang J. Organomet. Chem. 690 2005 1705 1709
5. G. Axelrad, S. Laosooksathit, and R. Engel J. Org. Chem. 46 1981 5200 5204
6. G. Axelrad, S. Laosooksathit, and R. Engel Synth. Commun. 10 1980 933 937
7. B. Åkermark, J.E. Nystroem, T. Rein, J.-E. Baeckvall, P. Helquist, and R. Aslanian Tetrahedron Lett. 25 1984 5719 5722
8. L.B. Han, Y. Ono, and H. Yazawa Org. Lett. 7 2005 2909 2911
9. L.B. Han, and M. Tanaka J. Am. Chem. Soc. 118 1996 1571 1572
10. A.A. Azab, A. Al Aziz Quntar, T. Abed, and M. Srebnik Heterocycles 82 2010 417 429
11. I. Zgani, C. Menut, M. Seman, V. Gallois, V. Laffont, J. Liautard, J.P. Liautard, M. Criton, and J.L. Montero J. Med. Chem. 47 2004 4600 4612
12. E. Villemin, B. Elias, R. Robiette, M.F. Herent, J.L. Habib-Jiwan, and J. Marchand-Brynaert Tetrahedron Lett. 52 2011 5140 5144
13. J.C. Monbaliu, E. Villemin, B. Elias, and J. Marchand-Brynaert O.A. Attonasi, D. Spinelli, Target in Heterocyclic Systems (THS) Vol. 14 2010 49 79
14. E. Villemin, and J. Marchand-Brynaert Synthesis 44 2012 1923 1927
15. E. Villemin, M.-F. Herent, and J. Marchand-Brynaert Eur. J. Org. Chem. 31 2012 6165 6178
16. T.W. Greene Protecting Groups in Organic Synthesis 1980 J. Wiley&Sons New York, NY
17. F. Eckstein Protection of Phosphoric and Related Acid J.F.W. Mc Omie, Protective Groups 1973 Plenum New York and London 217 234 Chapter 6
18. P.J. Kocienski Protecting Groups 3rd ed. 2005 Georg Thieme Stuttgart
19. C.E. Mc Kenna, M.T. Higa, N.H. Cheung, and M.-C. Mc Kenna Tetrahedron Lett. 18 1977 155 158
20. J.A. Goldstein, C.E. McKenna, and F.H. Westheimer J. Am. Chem. Soc. 98 1976 7327 7332
21. D.H. Rammler, L. Yengoyan, A.V. Paul, and P.C. Bax Biochemistry 6 1967 1828 1837
22. M. Kamber, and G. Just Can. J. Chem. 63 1985 823 827
23. F. Guibé Tetrahedron 54 1998 2967 3042
24. F. Eckstein, and I. Rizk Angew. Chem., Int. Ed. Engl. 79 1967 695 696
25. R.L. Letsinger, and W.B. Lunsford J. Am. Chem. Soc. 98 1976 3655 3661
26. H.-G. Chao, M.S. Bernatowicz, P.D. Reiss, and G.R. Matsueda J. Org. Chem. 59 1994 6687 6691
27. A. Sawabe, S.A. Filla, and S. Masamune Tetrahedron Lett. 33 1992 7685 7686
28. F.A. Atherton, H.T. Openshaw, and A.R. Todd J. Chem. Soc. 1945 382 385
29. A.R. Todd Angew. Chem. 60A 1948 69 70
30. J.C. Monbaliu, and J. Marchand-Brynaert Synthesis 11 2009 1876 1880
31. L. Saady, C. Lebeau, and Mioskowski Tetrahedron Lett. 36 1995 5183 5186
32. J.C. Monbaliu, J. Marchand-Brynaert, and B. Tinant J. Org. Chem. 75 2010 5478 5486
33. W.S. Wadsworth, and W.D. Emmons J. Am. Chem. Soc. 1961 1733 1738
34. T.L. Huller Tetrahedron Lett. 49 1967 4921 4923
35. M. Rambaud, A. del Vecchio, and J. Villieras Synth. Commun. 14 1984 833 841
36. O.E.O. Hormi, E.O. Pajunen, A.K.C. Avall, and P. Pennanen Synth. Commun. 20 1990 1865 1867
37. K.A. Petrov, V.A. Chauzov, and S.V. Agafonov Usp. Khim. 51 1982 412 437
38. P.C.B. Page, M.J. McKenzie, and J.A. Gallagher J. Org. Chem. 66 2001 3704 3708
39. K.A. Keller, J. Guo, S. Punna, and M.G. Finn Tetrahedron Lett. 46 2005 1181 1184
40. J.C. Cheronis, E.T. Whalley, K.T. Nguyen, E.D. Eubanks, L.G. Allen, M.J. Duggan, S.D. Loy, K.A. Bohnan, and J.K. Blodgett J. Med. Chem. 35 1992 1563 1572
41. C.E. Griffin, and W.M. Daniewski J. Org. Chem. 35 1970 1691 1693
42. Jaguar Version 7.5 2008 Schrödinger, LLC New York, NY
43. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
44. M.M. Francl, W.J. Pietro, W.J. Hehre, J.S. Binkley, M.S. Gordon, D.J. DeFrees, and J.A. Pople J. Chem. Phys. 77 1982 3654 3665
45. W.J. Hehre, R. Ditchfield, and J.A. Pople J. Chem. Phys. 56 1972 2257 2261
46. S. Grimme J. Comput. Chem. 27 2006 1787 1799
47. F. Neese ORCA, An Ab Initio, DFT, and Semienpirical Electronic Structure Package, Version 2.7.0 2010 Universität Boon Germany
48. G.M. Sheldrick Acta Crystallogr. A64 2008 112 122
49. J. Beck, L. Maton, J.L. Habib Jiwan, and J. Marchand-Brynaert Amino Acids 40 2011 679 689