6402
M. Funck et al. / Tetrahedron Letters 51 (2010) 6399–6402
24. Compound 11: yield 84%; 1H NMR (DMSO-d6; 400 MHz) d 2.49 (s, 12H), 4.83 (s,
4H), 5.96 (s, 4H), 6.59 (m, 4H), 6.69 (m, 8H), 6.95 (m, 4H), 7.55 (s, 12H) ppm; 13
NMR (DMSO-d6; 100.6 MHz) d 18.9, 120.5, 121.0, 124.3, 124.4, 128.9, 135.2,
References and notes
C
1. Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J. C.;
Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305–1312.
2. Paek, K.; Ihm, H.; Yun, S.; Lee, H. C.; No, K. T. J. Org. Chem. 2001, 66, 5736–5743.
3. Purse, B. W.; Rebek, J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 10777–10782.
4. Sliwa, W.; Deska, M. Chem. Heterocycl. Compd. 2002, 38, 646–667.
5. Atwood, J. L.; Barbour, L. J.; Jerga, A. Chem. Commun. 2001, 2376–2377.
6. Dalgarno, S. J.; Szabo, T.; Siavosh-Haghighi, A.; Deakyne, C. A.; Adams, J. E.;
Atwood, J. L. Chem. Commun. 2009, 1339–1341.
7. Kulikov, O. V.; Rath, N. P.; Zhou, D.; Carasel, I. A.; Gokel, G. W. New J. Chem.
2009, 33, 1563–1569.
8. Dalgarno, S. J.; Power, N. P.; Atwood, J. L. Coord. Chem. Rev. 2008, 252, 825–841.
9. Lutzen, A.; Hass, O.; Bruhn, T. Tetrahedron Lett. 2002, 43, 1807–1811.
10. Nikolelis, D. P.; Drivelos, D. A.; Simantiraki, M. G.; Koinis, S. Anal. Chem. 2004,
76, 2174–2180.
11. Vitovic, P.; Nikolelis, D. P.; Hianik, T. Biochim. Biophys. Acta, Rev. Biomembr.
2006, 1758, 1852–1861.
12. Leontiev, A. V.; Saleh, A. W.; Rudkevich, D. M. Org. Lett. 2007, 9, 1753–1755.
13. Ruderisch, A.; Iwanek, W.; Pfeiffer, J.; Fischer, G.; Albert, K.; Schurig, V. J.
Chromatogr., A 2005, 1095, 40–49.
14. Ruderisch, A.; Pfeiffer, J.; Schurig, V. J. Chromatogr., A 2003, 994, 127–135.
15. Sokoließ, T.; Menyes, U.; Roth, U.; Jira, T. J. Chromatogr., A 2002, 948, 309–319.
16. Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663–
2704.
17. Konishi, H.; Nakamura, T.; Ohata, K.; Kobayashi, K.; Morikawa, O. Tetrahedron
Lett. 1996, 37, 7383–7386.
139.8142.0, 142.3, 142.4, 142.9 ppm; MALDI-TOF
C56H48O12 m/z 935.97
[M+Na]+; elemental analysis for C56H48O12 calcd (found) C 73.67 (73.65), H
5.30 (5.30)%. Compound 12: yield 94%; 1H NMR (DMSO-d6; 400 MHz) d 2.39 (s,
12H, CH3), 4.96 (s, 4H), 6.23 (s, 4H), 7.00 (m, 12H), 7.43 (m, 4H), 7.55 (s, 12H)
ppm; 13C NMR (DMSO-d6; 100.6 MHz) d 19.6, 39.2, 124.7, 124.8, 126.1, 125.8,
129.6, 131.2, 137.0, 138.5, 143.0, 144.9 ppm; MALDI-TOF C56H48O12 m/z 935.97
[M+Na]+; elemental analysis for C56H48O12 calcd (found) C 73.67 (73.70), H
5.30 (5.30)%. Compound 13: yield 87%; 1H NMR (DMSO-d6; 400 MHz) d 1.49 (s,
12H), 4.96 (s, 4H), 6.17 (s, 4H), 6.89 (AA0XX0, 8H), 6.99 (AA ‘XX’, 8H) ppm; 13C
NMR (DMSO-d6; 100.6 MHz) d 19.1, 46.8, 120.0, 126.3, 127.0, 127.1, 129.8,
131.9, 140.3 ppm; MALDI-TOF
C
56H48O12 m/z 935.97 [M+Na]+; elemental
analysis for C56H48O12 calcd (found) C 73.67 (73.70), H 5.30 (5.30)%. Compound
14: yield 86%; 1H NMR (DMSO-d6; 400 MHz) d 2.49 (s, 12H), 5.22 (s, 4H), 5.67
(s, 4H), 6.14 (s, 4H), 6.68 (m, 12H), 6.72 (m, 4H), 6.53 (s, 8H) ppm; 13C NMR
(DMSO-d6; 100.6 MHz) d 20.7, 39.5, 103.1, 120.4, 121.1, 122.0, 125.8, 136.5,
136.7, 144.6, 145.8, 153.8 ppm; MALDI-TOF C56H48O8 m/z 848.33 [M+Na]+;
elemental analysis for C56H48O8 calcd (found) C 79.22 (79.22), H 5.70 (5.65)%.
Compound 15: yield 96%; 1H NMR (CDCl3; 400 MHz) d 1.35 (s, 12H), 4.87 (s,
4H), 5.36 (s, 4H), 5.44 (s, 4H), 6.75 (s, 4H), 6.84 (d, 3J = 7.73 Hz, 4H), 6.93 (d,
3J = 7.73 Hz, 4H), 7.07 (t, 4H, 3J = 7.44 Hz) ppm; 13C NMR (DMSO-d6;
100.6 MHz)
143.7, 150.9 ppm; MALDI-TOF
analysis for
d
19.7, 39.8, 100.7, 119.3, 123.7, 124.2, 127.9, 134.2, 138.9,
C
56H48O8 m/z 848.33 [M+Na]+; elemental
C56H48O8 calcd (found) C 79.22 (79.25), H 5.70 (5.70)%.
Compound 16: yield 94%; 1H NMR (CDCl3; 400 MHz) d 1.41 (s, 12H), 4.79 (s,
4H), 5.32 (s, 4H), 6.43 (s, 4H), 6.82 (AA0XX0, 8H), 6.95 (AA0XX0, 8H) ppm; 13C
NMR (DMSO-d6; 100.6 MHz) d 19.1, 39.6, 100.5, 119.2, 125.9, 127.0, 138.9,
18. Roberts, B. A.; Cave, G. W. V.; Raston, C. L.; Scott, J. L. Green Chem. 2001, 3, 280–
284.
19. Antesberger, J.; Cave, G. W. V.; Ferrarelli, M. C.; Heaven, M. W.; Raston, C. L.;
Atwood, J. L. Chem. Commun. 2005, 892–894.
20. Hedidi, M.; Hamdi, S. M.; Mazari, T.; Boutemeur, B.; Rabia, C.; Chemat, F.;
Hamdi, M. Tetrahedron 2006, 62, 5652–5655.
21. Yan, C.; Chen, W.; Chen, J.; Jiang, T.; Yao, Y. Tetrahedron 2007, 63, 9614–9620.
22. Cave, G. W. V.; Dalgarno, S. J.; Antesberger, J.; Ferrarelli, M. C.; McKinlay, R. M.;
Atwood, J. L. Supramol. Chem. 2008, 20, 157–159.
140.9, 150.8 ppm; MALDI-TOF
analysis for C56H48O8 calcd (found) C 79.22 (79.20), H 5.70 (5.70)%.
25. Crystal data of 3: C55H89O17.50S5.50, M = 1206.59 g molꢀ1, triclinic, space group P1
(No. 2), a = 12.7282(3) Å, b = 13.3196(2) Å, c = 19.2932(3) Å, = 104.3940(10)°,
= 99.0330(10)°, V = 3079.26(10) Å3, T = 120(2) K, Z = 2,
C
56H48O8 m/z 848.33 [M+Na]+; elemental
ꢀ
a
b = 97.5090(10)°,
Dc = 1.301 g cmꢀ3
c
l
,
= 0.272 mmꢀ1
,
F000 = 1294, crystal size = 0.19 ꢁ 0.17 ꢁ
0.08 mm3, R1 = 0.0780, wR2 = 0.1859, GooF = 1.015 Crystallographic data have
been deposited with the Cambridge Crystallographic Data Centre as
supplementary publication no. CCDC 755190.
23. Cave, G. W. V.; Jochen, A.; Barbour, L. J.; McKinlay, R. M.; Atwood, J. L. Angew.
Chem., Int. Ed. 2004, 43, 5263–5266.
26. Jachuck, R. J. J.; Selvaraj, D. K.; Varma, R. S. Green Chem. 2006, 8, 29–33.