V. Beejmohun et al. / Tetrahedron Letters 45 (2004) 8745–8747
8747
In summary, the monolignol glucosides (1,2-13C2)-p-
glucocoumaryl alcohol, (1,2-13C2)-coniferin and
(1,2-13C2)-syringin and their acid precursors have been
prepared for the first time.
7. Terashima, N.; Seguchi, Y.; Robert, D. Holzforschung
1991, 45, 35–39.
8. Newman, J.; Rej, R. N.; Just, G.; Lewis, N. G. Holzfors-
chung 1986, 40, 369–373.
9. Matsui, N.; Fukushima, K.; Yasuda, S.; Terashima, N.
Holzforschung 1996, 50, 408–412.
10. Fuchs, W. Chem. Ber. 1955, 88, 1825–1827.
11. Kratzl, K.; Billek, G. Monatsh. Chem. 1953, 84, 406–414.
12. Kratzl, K.; Billek, G. Holzforschung 1953, 7, 66–70.
13. Terashima, N.; Ralph, S. A.; Landucci, L. L. Holzfors-
chung 1996, 50, 151–155.
Acknowledgements
This work was carried out with the financial contribu-
´
tion of the Conseil Regional de Picardie (Pole IBFBio).
V.B. thanks the Conseil Regional de Picardie for a
ˆ
14. All new compounds were characterized byspectroscopical
methods. Analytical data for compound 4c: mp 253–
254°C; [a]D ꢀ13 (c 0.04, CH3OH); 1H NMR (300MHz,
´
fellowship. We thank Serge Pilard of the Plateforme
´
Analytique of the Universite de Picardie ÔJules VerneÕ
for mass spectrometryexperiments.
CD3OD): d 7.35 (ddd, 1H, J2,3 = 15.9, J3, C-1 = 6.0, J3, C-2
=
2.5Hz, H-3), 6.88 (s, 2H, H-20, H-60), 6.48 (ddd, 1H,
J2, C-1 = 2.7, J2, C-2 = 155.6Hz, H-2), 4.93 (d, 1H,
00
00 00
J1 ,2 = 7.3Hz, H-1 ), 3.88 (s, 6H, 2CH3O–), 3.79 (dd,
00 00
1H, J5 ,6 a = 2.5, J6 a,6 b = 12.0Hz, H-600a), 3.68 (dd, 1H,
00 00
References and notes
00
00
J5 ,6 b = 4.9Hz, H-600b), 3.50–3.40 (m, 3H, H-200, H-300, H-
00 00
1. Beutner, K. R.; von Krogh, G. Semin. Dermatol. 1990, 9,
148–151.
400), 3.23 (ddd, 1H, J4 ,5 = 7.3Hz, H-500). 13C NMR d
175.33 (d, J1,2 = 67Hz, C-1), 126.06 (d, C-2). ESMS
12
2. Thompson, L. U.; Seidl, M. M.; Rickard, S. E.; Orcheson,
L. J.; Fong, H. H. S. Nutr. Cancer 1996, 26, 159–165.
3. Croteau, R.; Kutchan, T. M.; Lewis, N. G. In Biochem-
istry and Molecular Biology of Plants; Buchanan, B.,
Gruissem, R., Jones, P., Eds.; American Societyof Plant
Physiologists, 2000; pp 1250–1302.
4. Seidel, V.; Windho¨vel, J.; Eaton, G.; Alfermann, A. W.;
Arroo, R. R. J.; Medarde, M.; Petersen, M.; Woolley, J.
G. Planta 2002, 215, 1031–1039.
5. Ford, J. D.; Huang, K.-S.; Wang, H.-B.; Davin, L. B.;
Lewis, N. G. J. Nat. Prod. 2001, 64, 1388–1397.
6. Gross, C. G. In Biosynthesis and Biodegradation of Wood
Components; Higuchi, T., Ed.; Academic Press:
New York, 1985; pp 229–271.
(+Na): Calcd for
Found: 411.1189.
C
13C2H22O10Na: m/z 411.1178.
15
15. Analytical data for compound 5c: syrup; [a]D ꢀ2 (c 0.07,
CH3OH); 1H NMR (300MHz, CD3OD): d 6.75 (s, 2H,
H-20, H-60), 6.55 (ddd, 1H, J2,3 = 16.0, J3, C-1 = 6.0Hz,
J3, C-2 = 3.0Hz, H-3), 6.11 (dddt, 1H, J1,2 = 4.0, J2, C-1
00 00
=
2.5, J2, C-2 = 154.0Hz, H-2), 4.90 (d, 1H, J1 ,2 =7.3Hz, H-
100), 4.22 (br dt, 2H, J1, C-1 = 142.0, J1,2 = J1, C-2 = 4.3Hz,
00 00
H-1), 3.83 (s, 6H, 2CH3O–), 3.78 (dd, 1H, J5 ,6 a = 2.5,
00
J6 a,6 b = 12.0Hz, H-600a), 3.68 (dd, 1H, J5 ,6 b = 5.1Hz,
00
00 00
H-600b), 3.45–3.35 (m, 3H, H-200, H-300, H-400), 3.20 (m, 1H,
H-500). 13C NMR d 130.05 (d, J1,2 = 47Hz, C-2), 61.56 (d,
13C2H24O9Na: m/z
12
C
C-1). ESMS (+Na): Calcd for
397.1385. Found: 397.1394.
15