Two novel acetophenones, 4-(1′-geranyloxy)-2,6-dihydroxyacetophenone 1 and 4-(1′-farnesyloxy)-2,6-dihydroxy-acetophenone 2 isolated from the fruit of Evodia merrillii and from the aerial parts of Borronia ramosa respectively, have been synthesized starting from 2,4,6-trihydroxyacetophenone 3; the key step in their total synthesis is the regioselective alkenylation onto the intermediate 6 with alkenyl bromide.
References
1.
EllisG. P., Chromenes, Chromanones and Chromones, John Wiley and Sons, New York, 1977; J. B. Harborne, The Flavonoids: Advances in Research since 1980, Chapman and Hall, New York, 1988.
2.
FukuiH., EgawaH., KoshimizuK., and MitsuiT., Agric. Biol. Chem., 1973, 37, 417; W. S. Bowers, T. Ohta, J. S. Cleere and P. A. Marseilla, Science, 1976, 193, 542; W. R. Phillips, N. J. Baj, A. A. L. Gunatilaka and D. G. I. Kingston, J. Nat. Prod., 1996, 59, 495; M. L. Barrett, A. M. Scott and F. J. Evans, Experientia, 1986, 42, 452; R. K. Razdan, W. R. Thompson, H. G. Parks and F. E. Gramchelli, Tetrahedron Lett., 1967, 3405.
3.
ChouC. J., LinI. C., and ChenC. F., J. Nat. Prod., 1992, 55, 795.
4.
MoniraA., AlexanderI. G., and PeterG. W., J. Nat. Prod., 1994, 57, 673.
