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C. Tang et al. / Tetrahedron Letters 52 (2011) 3275–3278
64, 217; (c) Buttner, F.; Bergemann, S.; Guenard, D.; Gust, R.; Seitz, G.; Thoret, S.
J = 7.7 Hz, 2H), 1.26 (t, J = 7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) d 167.1, 159.8,
147.4, 147.1 142.2, 140.4, 134.2, 129.7, 128.6, 123.3, 120.9, 114.4, 111.6, 110.3,
108.1, 101.1, 61.0, 55.2, 35.7, 14.3; ESI-MS m/z 341.2 [M+H]+; HR-MS(ESI) m/z
calcd for C20H20O5: 340.1318; found: 340.1305.
Bioorg. Med. Chem. 2005, 13, 3497; (d) Nakagawa-Goto, K.; Jung, M. K.; Hamel,
E.; Wu, C. C.; Bastow, K. F.; Brossi, A.; Ohta, S.; Lee, K. H. Heterocycles 2005, 65,
541.
3. Lin, R. J.; Cheng, M. J.; Huang, J. C.; Lo, W. L.; Yeh, Y. T.; Yen, C. M.; Lu, C. M.;
Chen, C. Y. J. Nat. Prod. 2009, 72, 1816.
4. Leblanc, M.; Fagnou, K. Org. Lett. 2005, 7, 2849.
12. Ester 5: white solid; mp 97–99 °C; IR (KBr) 2958, 2924, 2843, 1710, 1607, 1501,
1483, 1433, 1309, 1273, 1256, 1233, 1178, 1154, 1122, 1097, 1042, 933, 868,
815, 771, 739 cmÀ1 1H NMR (300 MHz, CDCl3) d 7.40 (d, J = 8.52 Hz, 1H), 7.27
;
5. (a) Wu, T. R.; Chong, J. M. Org. Lett. 2006, 8, 15; (b) Broady, S. D.; Golden, M. D.;
Leonard, J.; Muir, J. C.; Maudet, M. Tetrahedron Lett. 2007, 48, 4627; (c) Sawyer,
J. S.; Macdonald, T. Tetrahedron Lett. 1988, 38, 4839.
6. Seganish, W. M.; Deshong, P. Org. Lett. 2006, 8, 3951.
7. Djurdjevic, S.; Green, J. R. Org. Lett. 2007, 9, 5505.
8. (a) Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.;
Oka, S. J. Am. Chem. Soc. 1994, 116, 3684; (b) Kita, Y.; Tohma, H.; Inagaki, M.;
Hatanaka, K.; Yakura, T. Tetrahedron Lett. 1991, 32, 4321; (c) Dohi, T.; Ito, M.;
Yamaoka, N.; Morimoto, K.; Fujioka, H.; Kita, Y. Tetrahedron 2009, 65, 10797.
9. (a) Besong, G.; Jarowicki, K.; Kocienski, P. J.; Sliwinski, E.; Boyle, F. T. Org.
Biomol. Chem. 2006, 4, 2193; (b) Kita, Y.; Takada, T.; Mihara, S.; Tohma, H.
Synlett 1995, 211; (c) Kita, Y.; Takada, T.; Mihara, S.; Whelan, B. A.; Tohma, H. J.
Org. Chem. 1995, 60, 7144; (e) Arisawa, M.; Ramesh, N. G.; Nakajima, M.;
Tohma, H.; Kita, Y. J. Org. Chem. 2001, 66, 59.
(t, J = 6.5 Hz, 1H), 7.05 (s, 1H), 7.02 (s, 1H), 6.85 (q, J = 2.3 Hz, 1H), 6.77 (d,
J = 2.0 Hz, 1H), 6.01 (d, J = 4.0 Hz, 2H), 4.19 (q, J = 7.1 Hz, 2H), 3.82 (s, 3H), 3.22
(dd, J = 12.1, 8.4 Hz, 1H), 2.84 (dd, J = 12.1, 7.0 Hz, 1H), 1.27 (t, J = 7.1 Hz, 3H);
13C NMR (75 MHz, CDCl3) d 166.9, 159.3, 146.9, 145.7, 141.7, 140.1, 134.8,
131.3, 130.9, 130.5, 126.6, 112.2, 111.9, 109.6, 108.9, 101.2, 60.9, 55.3, 33.6,
14.2; EI-MS m/z 339.2 [M+]; HR-MS(ESI) m/z calcd for C20H18O5: 338.1157;
found: 338.1148.
13. Moreno, I.; Tellito, I.; Etayo, J.; Sanmartin, R.; Doninguez, E. Tetrahedron 2001,
57, 5403.
14. Tenuifolin (4): white solid; mp 116–119 °C; IR (KBr) 3319, 2961, 2924, 2861,
1720, 1606, 1501, 1483, 1401, 1307, 1275, 1258, 1231, 1154, 1121, 1039, 930,
748 cmÀ1 1H NMR (300 MHz, CDCl3) d 7.38 (d, J = 8.5 Hz, 1H), 7.13 (s, 1H). 7.07
;
(s, 1H), 6.83 (q, J = 2.5 Hz, 1H), 6.76 (d, J = 2.2 Hz, 1H), 6.16 (t, J = 7.1 Hz, 1H),
6.02 (d, J = 1.9 Hz, 2H), 4.48 (d, J = 12.8 Hz, 1H), 4.32 (d, J = 12.8 Hz, 1H), 3.83 (s,
3H), 3.08 (dd, J = 12.6, 8.2 Hz, 1H), 2.77 (dd, J = 12.8, 6.5 Hz, 1H); 13C NMR
(75 MHz, CDCl3) d 159.2, 146.4, 143.6, 137.4, 134.6, 131.2, 130.6, 129.8, 127.6,
111.7, 111.5, 109.5, 106.0, 101.2, 66.1, 55.3, 33.1; EI-MS m/z 297.2 [M+H]+; HR-
MS(ESI) m/z calcd for C18H16O4: 296.1052; found: 296.1043.
10. Ianni, A.; Waldvogel, S. R. Synthesis 2006, 13, 2103.
11. Z-6: coloress oil; IR (KBr) 2985, 2938, 2896, 2831, 1711, 1600, 1584, 1503,
1489, 1437, 1369, 1259, 1235, 1149, 1101, 1038, 935, 865, 812, 764, 749,
697 cmÀ1 1H NMR (300 MHz, CDCl3) d 7.26–7.11 (m, 2H), 6.82 (d, J = 7.9 Hz,
;
1H), 6.77-6.67 (m, 5H), 5.98 (s, 2H), 4.20 (q, J = 7.1 Hz, 2H), 3.79 (s, 3H), 3.41 (d,