Keywords
Leguminosae
deoxybenzoin
How to Cite
Abstract
In this paper we describe the synthesis of 2 ́,4 ́-dimethoxy-8-(propyl-2-one)-deoxybenzoin, anew compound employed as a model for the comparison with the respective spectral data for 6’,4-
dihydroxy-3’-(3,3- dimethylallyl)-2",2"-dimethylchromene(5",6":5’,4’)-2’-methoxy-8-(propyl-2-one)
deoxybenzoin, recently isolated from Deguelia hatschbachii A.M.G. Azevedo. Both compounds have a
“propyl-2-one” group attached to C-8 of the deoxybenzoin skeleton, for which there is no precedent in
the literature. The Friedel-Crafts reaction of 1,3-dimethoxybenzene with phenylacetyl chloride furnished
2 ́,4 ́-dimethoxydeoxybenzoin, that after reaction with allyl bromide gave 2 ́,4 ́-dimethoxy-8-(allyl)-
deoxybenzoin. Wacker oxidation gave the desired model compound in 15% overall yield. The corresponding
spectral data reinforced the structure previously determined for the natural product.
References
A. F. Magalhães, A. M. G. A. Tozzi, E. G. Magalhães, V. R.
S. Moraes, Phytochem. 57(1) (2001), 77.
F. E. King, T. J. King, A. J. Warwick, J. Chem. Soc. 96
(1952), 1920.
B. C. B. Bezuidenhoudt, E. V. Brandt, D. G. Roux, P. H.
Van Rooyen, J. Chem. Soc. Perkin Trans I (1980), 2179.
B. C. B. Bezuidenhoudt, E. V. Brandt, D. G. Roux, J.
Chem. Soc.Perkin Trans I (1981), 263.
E. Wong, The isoflavonoids . In: J. B. Harborne, T. J. Mabry, H. Mabry, The Flavonoids. New York: Chapman and Hall,1975.
A. C. Jain, P. Paliwal, Indian J. Chem. 27B (1988), 985.
A. Salakka, K. Wähälä, J. Chem. Soc. Perkin Trans. I
(1999), 2601.
[ 8 ] F. Kiuchi, X. Chen, Y. Tsuda, Heteroc. 31(4) (1990), 629.
N. Devi, N. Jain, H. G. Krishnamurty, Indian J. Chem.
B (1993), 874.
F. A. S. Coelho, G. Diaz, Tetrahedron 58 (2002), 1647.
(Footnotes)
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