Y.-J. Zhang et al. / Tetrahedron 68 (2012) 7400e7407
7407
~
ꢁ
12. Morales-Serna, J. A.; García-Ríos, E.; Bernal, J.; Paleo, E.; Gavino, R.; Cardenas, J.
Synthesis 2011, 9, 1375e1382.
(300 MHz, CDCl3):
d
¼3.50e3.28 (m, 2H), 1.46e1.18 (m, 20H), 1.08 (d,
J¼6.1 Hz, 6H), 0.87 (t, J¼5.7 Hz, 6H);13C NMR (75 MHz, CDCl3):
¼73.1,
d
13. Singh, K. N.; Kaur, A. Synth. Commun. 2005, 35, 2935e2937.
14. Suresh Babu, V. V.; Kantharaju; Sudarshan, N. S. Indian J. Chem. B Org. 2006, 45,
1880e1886.
37.7, 32.1, 29.6, 26.0, 22.8, 20.6, 14.2; GCeMS: tR¼9.75 min; m/z (%)¼
157 (28), 113 (60), 71 (100), 57 (86), 43 (90); Isomer 2: 13C NMR
15. Kim, H.-O.; Kahn, M. Synlett 1999, 1239e1240.
(75 MHz,CDCl3):
tR¼9.58 min; m/z (%)¼157 (32), 113 (73), 71 (100), 57 (87), 43 (68).
d
¼73.6,37.4, 30.3, 29.6, 27.0,25.8,21.2,14.2;GCeMS:
16. Tale, R. H.; Patil, K. M.; Dapurkar, S. E. Tetrahedron Lett. 2003, 44, 3427e3428.
17. (a) Soai, K.; Yokoyama, S.; Mochida, K. Synthesis 1987, 647e648; (b) Naqvi, T.;
Bhattacharya, M.; Haq, W. J. Chem. Res., Synop. 1999, 424e425; (c) Papavassi-
lopoulou, E.; Christofis, P.; Terzoglou, D.; Minakakis, P. M. Tetrahedron Lett. 2007,
48, 8323e8325.
18. Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395e4396.
19. Kokotos, G.; Noula, C. J. Org. Chem. 1996, 61, 6994e6996.
20. (a) Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993,
409e410; (b) Herbert, J. M.; Hewson, A. T.; Peace, J. E. Synth. Commun. 1998, 28,
823e832.
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S.; Heitz, A.; Martinez, J. Tetrahedron Lett. 1991, 32, 923e926; (c) Bandgar, B. P.;
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1993e1994.
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Org. Process Res. Dev. 2010, 14, 484; (c) Motoyama, Y.; Aoki, M.; Takaoka, N.;
Aoto, R.; Nagashima, H. Chem. Commun. 2009, 1574e1576.
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25. Breeden, S. W.; Lawrence, N. J. Synlett 1994, 833e835.
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2011, 3178e3183.
4.5.7. 1,10-Oxybis-cyclohexane (28b). Colorless oil; yield: 97%; TLC:
Rf¼0.75 (cyclohexane/EtOAc¼15:1); 1H NMR (300 MHz, CDCl3):
d
¼3.35e3.12 (m, 2H), 1.88e1.74 (m, 4H), 1.72e1.59 (m, 4H),
1.54e1.40 (m, 2H), 1.27e1.04 (m, 10H); 13C NMR (75 MHz, CDCl3):
d
¼74.6, 33.3, 25.9, 24.5; GCeMS: tR¼8.29 min; m/z (%)¼182 (16)
[Mþꢃ], 100 (100), 82 (100), 67 (34), 55 (86).
4.5.8. 3,11,19-Trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-
1(25),5,7,9(27),13,15,17(26),21,23-nonaene (29b). White solid; yield:
81%; TLC: Rf¼0.64 (cyclohexane/EtOAc¼5:1); 1H NMR (300 MHz,
CDCl3):
d
¼7.62 (s, 3H), 7.23 (dd, J¼8.5, 6.4 Hz, 3H), 7.17e7.12 (m,
6H), 4.50 (s, 12H); 13C NMR (75 MHz, CDCl3):
d
¼138.9, 128.3, 127.1,
127.0, 71.8; HRESI MS: calcd for C24H24NaO3 ([MþNa]þ) 383.1623,
found 383.1588.
27. Smith, M. B.; March, J. March’s Advanced Organic Chemistry: Reactions Mecha-
Acknowledgements
nisms and Structure, 5th ed.; Wiley: New York, NY, 2001, pp 477e478.
ꢁ
ꢁ
28. (a) Barluenga, J.; Tomas-Gamasa, M.; Aznar, F.; Valdes, C. Angew. Chem., Int. Ed.
2010, 49, 4993e4996; (b) Mitchell, T. A.; Bode, J. W. J. Am. Chem. Soc. 2009, 131,
18057e18059; (c) Shintou, T.; Mukaiyama, T. J. Am. Chem. Soc. 2004, 126,
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5920e5922.
China Scholarship Council is warmly thanked for PhD grants to
ˇ
Y.-J.Z.. Financial support allocated in the frame of Rhone-Alps In-
ternational Mobility (MIRA) scholarship program is also gratefully
acknowledged. Generous funds from the National Natural Science
Foundation of China (Grant 21176076) and the Fundamental Re-
search Funds for the Central Universities (No. 2011M500069) are
warmly thanked.
29. (a) Doyle, M. P.; DeBruyn, D. J.; Kooistra, D. A. J. Am. Chem. Soc. 1972, 94,
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Supplementary data
ꢁ
Supplementary data associated with this article can be found in
These data include MOL files and InChiKeys of the most important
compounds described in this article.
30. (a) Petit, C.; Favre-Reguillon, A.; Mignani, G.; Lemaire, M. Green Chem. 2010, 12,
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