Abstract
Two variants of synthesis of resveratrol (3,5,4"-trans-trihydroxystilbene) from dimethyl ether and anisaldehyde were performed using the chromium η6-benzenetricarbonyl complex. The Wittig—Horner reactions or aldol condensation in four stages followed by demethylation by EtSLi were applied.
Similar content being viewed by others
References
V. N. Kalinin, Usp. Khim., 1987, 56, 1190 [Russ. Chem. Rev., 1987, 56, 682 (Engl. Transl.)].
L. S. Hegedus, in Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, 1994, Ch.10.
M. F. Semmelhack, in Comprehensive Organometallic Chemistry II, 12, Eds. E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon, New York, 1995, pp. 979, 1017.
K. Schogl, in Organometallics in Organic Synthesis 2, Eds. H. Werner and G. Erker, Springer-Verlag, Berlin-Hiedelberg, 1989, 63.
H.-G. Schmalz and S. Siegel, in Transition Metals for Fine Chemicals and Organic Synthesis, Eds. C. Bolm and M. Beller, VCH, 1998, 25.
H.-G. Schmalz, M. Arnold, J. Hollander, and J. W. Bats, Angew. Chem., 1994, 106, 77 [Angew. Chem., Int. Ed., 1994, 33, 109].
H.-G. Schmalz and K. Schellhaas, Angew. Chem., 1996, 108, 2277 [Angew. Chem., Int. Ed., 1996, 35, 2146].
H.-G. Schmalz, A. Majdalani, T. Geller, J. Hollander, and J. W. Bats, Tetrahedron Lett., 1995, 36, 4777.
H.-G. Schmalz and K. Schellhaas, Tetrahedron Lett., 1995, 36, 5511.
H.-G. Schmalz, S. Siegel, and A. Schwarz, Tetrahedron Lett., 1996, 37, 2947.
H.-G. Schmalz, T. Volk, D. Bernicke, and S. Huneck, Tetrahedron, 1997, 53, 9219.
N. A. Tyukavkina, A. S. Gromova, V. I. Lutskii, and V. K. Voronov, Khim. Prirod. Soedin., 1972, 11, 600 [Chem. Nat. Compd., 1972, 8, 570 (Engl. Transl.)].
E. Mannila, A. Talvitie, and E. Kolehmainen, Phytochemistry, 1993, 33, 813.
M. Jang, L. Cai, G. O. Udeani, K. V. Slovink, C. F. Thomas, C. W. W. Beecher, H. H. S. Fong, N. R. Farnsworth, A. D. Kinghorn, R. G. Metha, R. C. Moon, and J. M. Pezutto, Science, 1997, 275, 218.
M. Fontecave, M. Lepoivre, E. Elleingand, C. Gerez, and O. Guittet, FEBS Letters, 1998, 421, 277.
V. Pont and R. Pezet, J. Phytopathol., 1990, 130, 1.
D. R. Kanis, M. A. Ratner, and T. J. Marks, J. Am. Chem. Soc., 1992, 114, 10338.
E. O. Fischer and K. Ofele, Z. Naturforsch. B., 1958, 13, 458.
C. A. L. Mahaffy and P. L. Pauson, Inorganic Synthesis, 1979, 19, 154.
S. G. Davies and T. D. McCarthy, in Comprehensive Organometallic Chemistry II, 12, Eds. E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon, Oxford, 1995, 1039.
M. Hudecek and S. Toma, J. Organomet. Chem., 1990, 393, 115.
R. Bajaj, M. T. Gill, and J. L. McLaughlin, Rev. Latinoamer. Quim., 1987, 18, 79.
H. Meier and U. Dullweber, J. Org. Chem., 1997, 62, 4821.
E. Alonso, D. J. Ramon, and M. Yus, J. Org. Chem., 1997, 62, 417.
M. A. Ali, K. Kondo, and Y. Tsuda, Chem. Pharm. Bull., 1992, 40, 1130.
M. Moreno-Manas and R. Pleixats, Anal. Quim., 1985, 81, 157.
P. Jeandet, R. Bessis, and G. Gautheron, Am. J. Enol. Vitic., 1991, 42, 41.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Polunin, K.E., Schmalz, HG. & Polunina, I.A. Chromium arene complexes in synthesis of trans-resveratrol. Russian Chemical Bulletin 51, 1319–1324 (2002). https://doi.org/10.1023/A:1020921101384
Issue Date:
DOI: https://doi.org/10.1023/A:1020921101384