3
1
2
3
4
5
6
7
8
9
Acknowledgment
59 12 S. Monge, B. Canniccioni, A. Graillot, J. J. Robin,
6
6
6
6
6
0
1
2
3
4
Biomacromolecules 2011, 12, 1973.
We thank the Tunisian Ministry of Higher Education and
Scientific Research for financial support.
Supplementary data
Supplementary data associated with this article can be found,
in the online version.
13
(a) T. Minami, T. Yamanouchi, S. Takenaka, I. Hirao,
Tetrahedron Lett. 1983, 24, 767. (b) H. Ding, G. Xu, J. Wang, Y.
Zhang, X. Wu, Y. Xie, Heteroatom Chem. 2004, 15, 549. (c) E.
Arce, M. Carmen Carreño, M. Belén Cid, J. L. Garcia Ruano,
Tetrahedron: Asymmetry 1995, 6, 1757. (d) M. Rambaud, A.
Vecchio, J. Villieras, Synthetic Commun. 1984, 14, 833.
(a) A. A. A. Quntar, M. Srebnik, Org. Lett. 2001, 3, 1379. (b) X.
Huang, C. Zhang, X. Lu, Synthesis 1995, 769. (c) L. -B. Han, Y.
Ono, H. Yazawa, Org. Lett. 2005, 7, 2909. (d) X. -N. Liu, W. -L.
Guo, C. -J. Hou, X. -P. Hu, Synthetic Commun. 2013, 43, 2622.
(e) C. Ma, X. Lu, Y. Ma, Main Group Met. Chem. 1995, 18, 391.
(f) C. Ma, X. Lu, Y. Ma Chin, Chem. Lett. 1995, 6, 747. (g) A.
Azab, A. A. A Quntar, T. Antebi, M. Srebnik, Heterocycles.
2010, 82, 417.
65
6
6
6
6
6
7
8
9
14
Supporting
Information
is
available
on
http://dx.doi.org/10.1246/cl.******.
1
0 References and Notes
70
7
7
7
7
7
7
7
7
7
8
8
8
8
8
8
8
8
8
8
9
9
9
9
9
9
9
9
9
9
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
1
(a) F. Fringuelli, A. Taticchi, Dienes in the Diels-Alder
Reaction. Wiley: New York; 1990. (b) B. M. Trost, A. B.
Pinkerton, M. Seidel, J. Am. Chem. Soc. 2001, 123, 12466.
(c) T. Miura, M. Morimoto, M. Yamauchi, M. Murakami,
J. Org. Chem. 2010, 75, 5359. (d) A. Lishchynskyi, K.
Muñiz, Chem. Eur. J. 2012, 18, 2212. (e) M. Ameur, A.
Arfaoui, J. Ben Kraïem, S. S. Al-Deyab, H. Amri,
Mediterr. J. Chem. 2012, 2, 347. (f) L. T. Kliman, S. N.
Mlynarski, G. E. Ferris, J. P. Morken, Angew. Chem. Int.
Ed. 2012, 51, 521. (g) S. Danishefsky, P. F. Schuda, T.
Kitahara, S. J. Etheredge, J. Am. Chem. Soc. 1977, 99,
6066.
15
16
17
B. Schmidt, O. Kunz, Org. Lett. 2013, 15, 4470.
P. Gangaram, M. Chakravarty, RSC Adv. 2013, 3, 20503.
(a) J. Á. Bisceglia, L. R. Orelli, Curr. Org. Chem. 2015, 19,
744. (b) Y. Aljasem, R. El-Esawi, T. Thiemann J. Chem.
Res. 2014, 38, 453. (c) J. Á. Bisceglia, L. R. Orelli, 2012,
16, 2206.
(a) A. Samarat, V. Fargeas, J. Villiéras, J. Lebreton, H.
Amri, Tetrahedron Lett. 2001, 42, 1273. (b) A. Samarat, Y.
Landais, H. Amri, Tetrahedron Lett. 2004, 45, 2049. (c) B.
Toumi, A. Samarat, A. Harizi, H. Amri, Phosphorus Sulfur
Silicon Relat. Elem. 2010, 185, 652.
18
19
2
(a) X. Zhang, R. C. Larock, Org. Lett. 2003, 5, 2993. (b) B. E.
Sime, B. Rickborn, J. M. Flournoy, I. B. Berlman, J. Org. Chem.
1988, 53, 4613. (c) M. DellaGreca, C. D. Marino, A. Zarrelli, B.
D’Abrosca, J. Nat. Prod. 2004, 67, 1492. (d) Y. Cheng, B.
Schneider, U. Riese, B. Schubert, Z. Li, M. Hamburger, J. Nat.
Prod. 2004, 67, 1854.
(a) The tetraethyl methylenediphosphonate
1
was
synthesized by slightly modified procedure from
a
literature as follow: A three-necked round bottomed flask
equipped with a magnetic stirrer, nitrogen sweep and
addition funnel was charged with anhydrous
dichloromethane (100 mL) and sodium (0.3 mol, 6.9 g). A
freshly distilled diethylphosphite (0.3 mol, 40 g) was
added dropwise at 0°C over 2 hours with continuous
stirring at 0°C for 48 hours. Then, the reaction was
vigorously stirred at room temperature for 12 days under
nitrogen atmosphere. The obtained blue reaction mixture
3
4
(a) A. Rybak, M. A. R. Meier, Green Chem. 2007, 9, 1356. (b)
A. Behr, J. P. Gomes, Beilstein J. Org. Chem. 2011, 7, 1.
(a) E. Borré, T. H. Dinh, F. Caijo, C. Crévisy, M. Mauduit,
Synthesis 2011, 2125. (b) J. Xu, E. J. E. C. Diaz, L. Trozoss, E. A.
Theodorakis, J. Am. Chem. Soc. 2012, 134, 5072. (c) J. S. Glasby,
Encyclopaedia of the Terpenoids, Wiley: UK.1982.
5
(a) J. A. M. Lummiss, K. C. Oliveira, A. M. T. Pranckevicius, A.
G. Santos, E. N. Dos Santos, D. E. Fogg, J. Am. Chem. Soc. 2012,
134, 18889. (b) G. Moura-Letts, D. P. Curran, Org. Lett. 2007, 9,
5.
was diluted with water (20 mL) and extracted with CHCl
(3 x 25 mL). The organic layers were dried over Na SO
3
2
4
and concentrated under vacuum. The residue was distilled
under reduced pressure to provide the tetraethyl
methylenediphosphonate 1 in a comparable yield (25 g,
6
7
8
P. Savignac, B. Iorga, Morden Phosphonate Chemistry; CRC
Press: Boca Raton, FL, 2003.
1
1
1
1
1
00
01
02
03
04
S. Montel, C. Midrier, J.–N. Volle, R. Braun, K. Haaf, L. Willms,
J. –L. Pirat, D. Virieux, Eur. J. Org. Chem. 2012, 17, 3237.
A. Gaynullin, N. Davletshina, R. Davletshin, A. Garifzyanov, R.
Cherkasov, Phosphorus Sulfur Silicon Relat. Elem. 2016, 191,
1666.
19b
58 %) to that reported by Hormi and co-workers. (b) O.
E. O. Hormi, E. O. Pajunen, A. K. C. Avall, P. Pennanen,
Synthetic
Commun.
1990,
20,
1865.
9
(a) T. Okauchi, T. Kakiuchi, N. Kitamura, T. Utsunomiya, J.
Ichikawa, T. Minami, J. Org. Chem. 1997, 62, 8419. (b) J. –C.
Monbaliu, B. Tinant, J. Marchand-Brynaert, J. Org. Chem. 2010,
75, 5478. (c) J. –C. Monbaliu, B. Tinant, J. Marchand-Brynaert,
Synthesis 2009, 1876. (d) E. Villemin, B. Elias, R. Robiette, K.
Robeyns, M. –F. Herent, J. –L. Habib-Jiwan, J. Marchand-
Brynaert, Tetrahedron Lett. 2011, 52, 5140. (e) T. Minami, S.
Tokumasu, R. Mimasu, I. Hirao, Chem. Lett. 1985, 14, 1099.
(a) V. Ojea, S. Conde, M. Ruiz, M. C. Fernandez, J. S. Quintela,
Tetrahedron Lett. 1997, 38, 4311. (b) M. Ruiz, V. Ojea, S.
Conde, J. S. Qrintela, Synthesis 2003, 689.
10
11
L. T. Burke, D. Dixon, S. V. Ley, F. Rodriguez, Org. Biomol.
Chem. 2005, 274.